Distributed, with Matt Mullenweg

Read more about the Grand Meetup in “The Importance of IRL in a World of Screens.”

On this episode of the Distributed podcast, we get an insider’s look at the Grand Meetup, Automattic’s annual weeklong all-staff event, where employees have an opportunity to collaborate, learn from one another, and hang out face-to-face. Folks from across the company share what makes this gathering so special, talk about social cohesion in the context of a large distributed company, and reflect on what’s great (and what’s tough) about the distributed lifestyle.

The full episode transcript is below.

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Mark Armstrong: Okay go.

Josepha: The song that’s in my head right now is “Good morning. Good morning.” My name is Josepha Haden Chomphosy. I shouldn’t say it like a question. That is my name. My name is Josepha.

Mark: Great to see you. Thank you for stopping by the Automattic podcast booth. Josepha what do you do with Automattic?

Josepha: Great question. A little bit of everything. I am the lead of the .Organization Division, which is the division that supports and helps to guide a lot of our open-source work with the WordPress project itself.

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Mark: Who are you? Tell me your name.

Aaron Douglas: My name is Aaron Douglas. I am a Mobile Wrangler for Automattic. My official job title is actually Chief Tater Tot Officer — I neglected to change that and it just stuck. I work on the WooCommerce mobile app as my primary thing, but everywhere around Automattic I try to help out where I can.

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Mark: OK. Here we are in the hallway again. What’s your name and what do you do at Automattic?

Brandon Kraft: Hi, I’m Brandon Kraft. I’m a Code Wrangler working with our Jetpack plugin.

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Mark: What is your name?

Sheri: Sheri Bigelow.

Mark: And what do you do at Automattic?

Sheri: I am an Excellence Wrangler.

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Rocío Valdivia: My name is Rocío Valdivia. I am from Spain and I’m a Community Wrangler at Automattic.

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Achaessa James: I’m Achaessa and I’m with the Legal team.

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Will Brubaker: So my name is Will Brubaker. I am the Chief Mechanical Officer.

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Erin Casali: So hello, I’m Erin Casali, often referred as “Folletto,” and I currently work as the Design Lead of Jetpack. And how long? It’s been a while now, six years.

Mark: Where are we now, here?

Erin: So we are — I think — in Orlando, because we are inside a hotel, and have been a while, so I’m not entirely sure where we are? Your hotels look all the same. But we’re in Orlando. I lost count of time. I think we are on day three or four of the Grand Meetup.

Mark: It really is a blur, isn’t it?

Erin: It is.

Mark: Thank you for being here.

Matt Mullenweg: Howdy howdy, I’m Matt Mullenweg, the CEO of Automattic, and the host of the Distributed podcast. Those voices you just heard? Those were Automatticians — folks who work for Automattic — and today we’re going to be hearing from them about this year’s Grand Meetup, and more broadly, what distributed work means to them. Back in September, Automattic held its annual Grand Meetup, which is the one time during the entire year that pretty much everyone at Automattic gets together in one place. The other 51 weeks of the year, we all work from different places all over the world — over 70 countries now. So this is a chance for some of us to meet face-to-face for the first time, and for everyone to catch up with old friends, discuss our work and align around our goals, and hear great talks from folks like Stephen Wolfram (who was a guest on this podcast a few weeks back). We set up a recording booth at the meetup and talked to a bunch of folks from around the company to hear about their experiences with distributed work. My colleagues Mark Armstrong and Ben Huberman were on the ground, asking questions throughout the meetup. Mark and Ben are from Automattic’s Editorial team, and they’ve also been helping out a ton with this podcast. We’ll kick things off with some Automatticians talking about why meetups matter for distributed teams, then get into an interview with Megan Marcel, our Director of Global Events & Sponsorships, about what it takes to pull off this huge event with so many people — I think we had around 900 this time. Then we’ll hear some remote work tips, and finish with some stories about why these folks have chosen the distributed lifestyle. OK, let’s do it. Take it away, Mark.

Mark: OK, thank you, Matt. Now that we’ve met some of our colleagues from Automattic, let’s go deeper and learn a little bit more about their experiences at the Grand Meetup. If I can set the scene a little bit, Ben and I stationed ourselves at different tables outside in the hallways of this conference room in Orlando — just a few miles from Walt Disney World. We just flagged down people as we saw them, or people would see us with a microphone and say, “Hey, what’s that? Can I get interviewed?” I have to say it was super fun to have an excuse to pull people aside and interview them and ask them about their experience at the Grand Meetup. It can be such a nerve-wracking experience to be surrounded by all the people you work with, so it’s just fun to take a step back and look at the scene, and ask some questions of each other on what it’s all about and why we’re even there in the first place. 

Mark: Now we’re here at the Grand Meetup in Orlando, Florida. What is the Grand Meetup?

Josepha: The Grand Meetup is basically like a company all-hands. I think that’s how corporate places call it, where we get everybody from the company who’s able and willing together in one place to do some additional training, additional team-building, and a lot of [the things that have] to happen when you work in a distributed company. So when you work in a distributed company, every time that you interact with your colleagues via text, or however you are away from them, you are taking out of your social bank account with them. And so when you get people together, that’s when you have the opportunity to see each other face to face, remind everybody that you’re all human beings, and fill that social capital back up, because it’s so hard to communicate via text. That’s one of the main benefits of bringing everybody together this way. Of course we have a lot of trainings and a lot of opportunities to have high-bandwidth conversations. But I think that’s one of the main benefits, and it’s almost a side-effect benefit. I don’t think anyone thinks actively about that when they bring everybody together for this.

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Mark: When did you join Automattic?

Achaessa: November 1 in 2018, so I give a flash talk this year. It’s my first GM.

Mark: Fantastic. So what how has it been so far? 

Achaessa: The GM? I love it. I love it. I’m meeting all these people who I’ve been working with all this time and it’s so awesome. It’s like the best in the world.

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Will: It’s a very energizing experience to be here. My job is very demanding, and my life is very demanding, and everything around us is very demanding. I start to get de-energized in about July or August, and it’s also like things are physically — it’s hot outside, and things are more difficult in this time of year, at least for me. But then I get here, and I get around people and I ask questions there that are on my mind and what I’m passionate about, and I want a real answer here. And you know what? I get a real answer, and I get an answer that inspires me and makes me want to go home and work harder. You know what? I’m empowered now to fix the things that have exhausted me, and we’re going to start over, and we’re going to move towards the next year’s goals, and I’m very clear what those are. And that’s what this does for me, is that it’s a reset. It energizes.

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Ben: So right now we are in Orlando for the annual Grand Meetup. What does the Grand Meetup mean to you?

Rocío Valdivia: Wow. The Grand Meetup means a lot of things to me. I love the energy. I come back home with all my batteries charged for the rest of the year. I’m very aligned with the values of this company and I’m very aligned with the kind of people that I find here in general. Nobody’s normal, right, and everybody’s different in so many different ways. And in this company you can be however you want to be, and [be] nice to each other. And something that I will highlight as well is that everybody helps each other. I love that. And what I value the most about the GM is the connections that I create in person, that I can use them. It’s like I take advantage of all the connections I create in person during the GM the rest of the year. I learn more what people do. For example, I sit down and I meet someone during lunch and hey, this person just tells me that [they] work in marketing or [they’re] working on this and that. And then we have a conversation and we realized that we have so many things in common. And then for example, I am marketing seeking help maybe with WordCamps, and then we start planning. “Oh we should do this. We should do that.” And I love it. Because normally those kinds of things don’t happen during the year because you are so focused on your daily-basis job that you can not find the time to just hang out in different teams’ channels. I don’t normally do it because [I am] so busy. Right?

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Mark: What was your first Grand Meetup like?

Josepha: Oh, my first Grand Meetup was terrifying. I’m a wild extrovert, especially compared to a distributed technology company standard-issue employee. Wild extrovert.

Mark: What are you talking about?

Josepha: “I’ve never heard of such a thing!” I was told by my team lead at the time that I didn’t need to prepare for anything because I was so extroverted. And so I arrived and I had no idea what to expect or who was there. I joined a tiny team — like seven people, maybe six even — and so I joined and I knew them and that was it. I didn’t know that there was this whole other company going on. I didn’t know that we had classes we had to attend. I just showed up to stuff randomly on the day that they were happening and it was really stressful. Even for me, I remember thinking at the end of it like, “I’m not sure that I’m an excellent fit here.” I wasn’t prepared. Everybody knows everyone. I don’t know anyone. I have nothing in common because of course I hadn’t spent any time trying to figure out where I was headed. It was really stressful. But I made it through.

Mark: It’s a sensory overload, isn’t it?

Josepha: Yeah. It’s like the first time you go to CES, in case anyone does. You can make it about two-and-a-half days before you’re like, “This is terrible and I’m going to hide in my room until everyone is gone. And then I’m going to get on the first very slow transportation out of here, and that’s it.”

Mark: But it’s like CES, but they are everyone you work with, and a bunch of people who you have already chatted with, but you have never met them in person.

Josepha: Exactly. Exactly. And you’re not sure whether you inadvertently offended them. And sometimes you completely forgot to respond to them cause you hadn’t figured out how to use all the communication channels yet. And they’re like, “I asked you something two months ago, it probably shouldn’t have been time sensitive, but now I’m mad and it is.” So you run into all these surprises because you hadn’t figured out how to communicate. You hadn’t figured out how to work with all of the information that comes in because there’s so much information all the time and you have to be proactive about finding it, which is good, in a way, and also really difficult in ways as well.

Mark: We’re in a big hotel complex in Orlando, Florida right now. We’ve got a bunch of employees in front of us. How does this compare to your first Grand Meetup?

Josepha: It was so much more casual, because, if you think about the difference between 300 employees to almost a thousand employees, and the types of employees, and the roles that they have — that we’ve taken on since then — it was so much more casual. It was almost familial before. And I don’t know if it’s mostly a matter of the way that my work has changed, but I remember that I was in full discovery mode the whole event and just trying to figure out who did what and why, and where all the work came from, and what we were doing, and why we did it. And now it feels like — and I don’t know if it’s accurate or not — but it feels like for the most part, everybody already knows where they’re supposed to be, what they’re supposed to be doing, how the work is supposed to go. We show up and everybody already has this excellent plan and a goal for what to do for the week, even if that goal is “finish my support rotation.” And I think that’s a really nice thing, to have a really easy, collegial sense, which before was a “Hey, casually figuring out what to do now that we’ve arrived.” 

Mark: Now there’s another element to Grand Meetups that continues to this day, although it’s evolved a bit. Your first Grand Meetup, correct me if I’m wrong, you did not know that you were going to have to present a flash talk?

Josepha: Yeah, I didn’t quite know. I had never seen a flash talk. I didn’t even do any research. So I arrived and someone had told me, “This is a thing that has to happen but it’s really easy, because you’re an extrovert, and so you show up and you talk for four minutes, it’ll be easy.” Now I love public speaking and I’ve done a lot of it, and four-minute presentations for me are way harder than 45 minutes, because you have to choose and plan what you’re going to say, every second of all of that. You don’t have any room for extemporaneous chatter. And so I showed up and they were like, “Oh we never received your slides.” And I was like, “What slides? Why do I need slides? What is it? What is the flash talk?” It’s short. I thought I just had to get up and say my name. And so I had to suddenly pull together slides and it was the most boring, bland title for a talk I could have ever imagined. It was like “Learning to be a better mentor,” which is super on-brand for me. And also, especially seeing what I do now, super on-brand for the future of my work here. But I didn’t know that at the time. No one else knew it at the time. I was just someone here to manage meetups. Man, I felt so stupid because everyone else is “Making paella the best: why Spaniards hate your stupid ham.” And mine was like, “Be a better mentor.” I was so serious. I showed up and I was serious and it was mildly embarrassing, but I survived.

Mark: I have to say, I think I remember watching your flash talk and saying, “Yes, Josepha is here.” I really enjoyed it. I remember enjoying it. Kudos to you.

Josepha: Thank you.

Mark: But it is a funny thing because you come in and you think the flash talks are going to be half about work or maybe some lighthearted stuff. But very rarely they’re about your day-to-day work. I have learned we have such a talented group of people at this company and that’s what I feel like I learned so much from these flash talks. People have such diverse interests and hobbies and passions.

Josepha: It brings back that human element, and humanizing people again and reminding people that we’re more than just a Happiness Engineer or someone on Editorial. There’s more to who we are than just that one thing. And I think that’s really special and really important and something you don’t get in corporate settings that are this size.

Mark: What are some other pro tips for attending a Grand Meetup? 

Josepha: I think the thing that is most important is to consider what your boundaries are before you come. It’s so easy for introverts and extroverts to get swept up in the excitement of it, and like — are you willing to stay up until two in the morning in the party suite? Because that’s where the people that you had dinner with ended up. Because if you don’t, you don’t prepare for it. If you normally go to bed at at 10 o’clock at night and wake up at 6:00 AM and have a really clear routine, and then you get so far off your routine because you’re so excited and you want to connect with people and learn more about them, you can really forget to prepare yourself for that and just wear yourself out long before the event is over. Because especially now, we have these really — this year we have these big Team Days for the first day-and-a-half, and then a bunch of individual trainings all the way through, and ways that people can learn and do high-level planning and teamwork throughout the week. You want to be remotely fresh all the way through that. And if you just don’t remember that you plan to be an extrovert this week and so your introverted self forgot to have lunch by yourself in your room, you’ll feel really overwhelmed by the end of it. And so just planning for that, knowing what you’re wanting to do and how it’s going to change your routine, and being mindful of that for yourself is the biggest thing I think anyone can do before they come.

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Mark: What’s been your favorite part of the Grand Meetup so far?

Brandon: That’s a hard question. There’s so many great parts of the Grand Meetup. In some sense we have some amazing keynote speakers. And hearing these folks that we would never meet in person otherwise, and having some really great insight there. But frankly, really it’s just this time here, like right down the hallway between sessions, being grabbed by you, Mark, just to talk for a few minutes. I really like that ability to meet with different people like that, that we wouldn’t normally ping each other on Slack because we don’t really have an operational reason to. But we know each other and we see each other and we rekindle that relationship, even though we don’t work together day-to-day. And if we never had the Grand Meetup, we wouldn’t be able to keep that going. I think the best part is just seeing people that I know from other parts of the company. And even if it’s just a quick hello, or a handshake, or a cup of coffee, or five minutes on a podcast. I really think that’s the most valuable part of the Grand Meetup.

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Mark: Now what are you doing this year? Are you doing a project?

Erin Casali: The last few years I’ve helped with organizing the classes. This year I just taught a couple of classes — well, more workshops. I prefer the full workshop format myself. And this year I was helping out with one on floor storming, which is a workshop technique to synchronize and discuss processes. We worked on one on fast design — how to generate ideas quickly, how to push ourselves to create wild ones that then can become useful to projects.

Mark: What else happens at a Grand Meetup?

Erin: A lot of things. This year is probably one of the most varied ones. So you have a combination of assigned tables, which is something that at the beginning you’re like, “Why are you assigning the table to me?” But then if you feel relaxed because you’re like, “Yeah, I know I need to go to the table, and I know it’s going to be all new people.” And so you chat, you know new people. And then there are keynotes, external speakers, and then there are projects. And then there are a lot of occasions to catch up with people and coordinate things. One of the most beautiful things is how some of the — in the free time between activities — how naturally some discussions pop up. For example, today I’m just out of a discussion that was organized one hour earlier. And because some teams felt the need to discuss some critical topics, some problems they found. And they pulled in the right people, and in an hour we were able to identify some problems, identify some steps forward. It’s still a challenge, but now everyone is synchronized. And it happened just because someone was like, “Yeah, let’s pull the right people in the room together.”

Mark: When you have something like that happen, do you sometimes ask yourself, “Why do we not get together more often?”

Erin: Frankly, I think there is a balance there. There are times when you’re like, “Oh, I really need to pull people together.” But remotely, you still can. Sometimes it’s just a matter of spinning up a remote chat and sometimes it’s also faster remotely because everyone’s just typing away. You send that private message and that’s very simple in a way. For me that’s one of the powerful — that is a bit understated when we talk about remote work because in practice, very few discussions actually require people to be there in person. What you need is people to synchronize, and there are many ways to synchronize. In this case, I think this could have happened digitally. But it’s just effective because we are here.

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Mark: How does it feel to you seeing the evolution of the company and the evolution of the Grand Meetup, for you to be in this giant hallway and surrounded by a thousand of your closest colleagues?

Sheri: It’s so many people. That’s really funny because I came into this meetup like, “Oh, Grand Meetups are not the same. It won’t be the same feeling anymore. This one, it’s too big now. It’s like I don’t know anyone anymore.” I’ll just be walking around and I won’t know anyone. I won’t see anyone that I know and how will that feel? And I thought “Oh, maybe it won’t be as good.” But when I got here, I found that I just see someone, I can’t move through the hall without stopping like 20 times. So it takes me really long to move from one place to the other because I recognize someone, I see someone I worked with, I see someone I’ve only met online ever before and I want to say hi to everyone. And so yet again I’m here saying “I love everyone,” but I haven’t met — I don’t think I could possibly meet them all, actually. There is some really nice balance for me in the sense that I can have some great deep conversations and see my teammates. There was time set up for teams in the beginning, which I greatly valued and that whole “this is massive” feeling, like, “Oh my gosh, look at this room that we filled with people who are my people. They’re just like me.” And that’s one of the things that I thought when I — the very first WordCamp San Francisco that I went to, I was like, “These people are just like me. These are my people.” I feel a strong connection and [hold] a special place in my heart for everyone before I even meet them because I know that if you work here you’re probably pretty great.

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Mark: Had you met any Automattic employee in person before the Grand Meetup?

Achaessa: In person before the Meetup? Yeah, a few.

Mark: So just to clarify, before you joined the company — the interview process, none of that was in-person, right?

Achaessa: No, none of it was in-person. None of it all. But I’ll tell you the reason that I even applied. So I saw this job posted — the corporate paralegal position posted. And I was like, who is this? What’s this company? And so I went and I did my homework and when I got to the HR page, there was the link to the Diversity and Inclusion videos. I went there and I started watching those videos and tears just started shooting out of my face. And I was like, these are my people. I don’t know, it’s just — every single one of them spoke to my heart. In 2016 I got laid off from a consulting job and I had to take an in-house job that required me to be in an office in San Francisco. And I will just tell you that I feel closer to the Automatticians than I felt to those people sitting next to me in that office. Because in an office, sometimes you form cliques and so — I’m 60. You can see my hair, you know, and these were all very young people and they were — they partied a lot. They were still in that age. I’ve been through that age, but I’m not there anymore. And so it was very hard for me to integrate myself in that community. But at Automattic we have interest groups, I guess you would call [them]. We have Slack channels for every level of interest, and I have never felt more included in my life. I have people coming up to me at the gym: “I know you from this channel,” “Oh yeah, I love what you said here,” “Are you going to do this?” And “Let’s do this!” It’s like coming to family, you know, it’s like a family reunion.

Mark: Tell me about your flash talk.

Achaessa: Ooh. Okay.

Mark: What is a flash talk?

Achaessa: So a flash talk every first year. Now I hear I lucked out because it used to be every single person, every single year had to do a flash talk until what year?

Mark: I would say that would have been 2016 or 2017…

Achaessa: I just lucked out. So now it’s every person at their first GM has to give a “Four minutes about me.” So whatever — not necessarily about you, but whatever you want to talk about, you’ve got, maximum, four minutes to do it. And I really freaked out at the beginning, which is funny because in my industry, equity comp, I do speaking engagements all the time. I used to run an education program. I did talking all the time. But this “four minutes about me” was just like, “Ugh.” But I did it. Well, I haven’t done it yet, but I prepared. I prepared my flash talk. It’s about aging and adventure. It’s called “When Does the Adventure End? 30? 40? 50? 60?”

Mark: Spoilers? Can you tell me when the adventure ends?

Achaessa: Never. It never ends. It absolutely never ends. It just depends on how you approach it, right?

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Mark: Now how does this compare to your very first meetup? When did you join Automattic?

Aaron: It was barely two months before the Grand Meetup. That was in San Francisco, and also Santa Cruz, California.

Mark: How many employees at the company at that time?

Aaron: Oh gosh. I think I was number 220 at that point. So it felt like a large company to me at that point, and having not come from the WordPress community. I’ve used WordPress, but I have an iOS developer background, some Android as well. My sphere did not include the community around WordPress, so I felt a bit out of sorts when I first came to the Grand Meetup because I felt like I didn’t belong. But it was maybe an hour in after sitting on the couch at the old Automattic headquarters that I immediately knew that I was at the right place, connecting with the people that were there and just felt very welcomed and included. I was already in on the jokes on day one, so it was great.

Mark: That’s fantastic. So how does the vibe compare, 220 employees, to — here we are with going on over a thousand employees?

Aaron: Realistically the vibe hasn’t changed all that much in my mind, because there aren’t that many times that you’re all together in the same room. So I will say that if we’re doing a major Town Hall or we’re doing a keynote and you happen to turn around, then yes, it’s very obvious that we’re a lot larger. I’m one of those people that tends to sit in the front row. So my perspective hasn’t changed all that much. When it comes to the hallway conversations, we tend to do training or classes — people hold classes for other Automatticians to teach their own things that they’ve learned. Those are still relatively the same size and those conversations haven’t really changed their format at all. So yes, we’ve grown in scale, but really the heart of what the annual Grand Meetup is, is still the same, at least in my mind.

Mark: Why, if you’re a distributed company, why would you have a Grand Meetup? Why would you do this every year?

Aaron: Financially it’s a hard hit on Automattic’s books because you’re flying everybody into the same space, you’re giving them a place to sleep, and feeding them fairly well, actually. But the reality is, it’s hard to quantify what the Grand Meetup gives us — in material things, swag, I guess we get. So that’s cool as an Automattician, but the reality is I’m developing relationships with people across Automattic that I may not have a chance to work with on a daily basis. I have not crossed paths with you all that much except for a few Editorial PR-related things. But we’ve had a ton of conversations at the GMs over the years and what I like to call — well we use Slack, so I’ll just say Slack. The Slack Effect is that, when I’ve met someone in person and I’ve heard their voice, and I’ve seen their eyes and their face. If I have further conversations with them after Grand Meetup, my brain has a hard time discerning whether or not the conversation happened in person or in a Slack or offline asynchronous manner.

Mark: So you’re able to project that personality in conversation under all sort of communication thereafter?

Aaron: Yep. If I’m reading a message from you, your personality bleeds through into how I’m interpreting things to be written. If I haven’t met someone yet, I have a general Automattician voice, [I] assume positive intent and all that. But I think it really helps make me not feel like I’m alone at my house when I have all the Automatticians’ voices, when I’m interacting with people through electronic means. So to me the Grand Meetup is essential for me to feel successful.

Mark: What tips would you give in terms of how to navigate the Grand Meetup?

Aaron: Listen to yourself. If you’re in a state where you are overwhelmed, or if there’s so much input — too many voices, too many smells, too many places to go — you feel like you’re being left out of things. It’s OK to just find a quiet place, sit for a bit, process your thoughts, and then continue on with the day. If you need to go hide in your room for a little while, that’s perfectly acceptable. It’s a lot to take in. You are quite literally, from waking up to going to bed, always subject to things happening. It could be meals, it could be keynotes, conversations in the hallway, and — we all work from home. We have a lot of control over our day and here you have to give up a little bit of that control, and that can be overwhelming, so, self care is really a big thing. The other tip that I would give any new Automattician is just to say hello. It’s amazing what I’ve been able to do by meeting people here at the Grand Meetup that I don’t normally work with on a daily basis. How that’s helped me even years later when, I do need to get something done for my job [that requires input from someone who] happens to work with a team that I haven’t been able to work with before. I can look at someone on a team — like, I had that conversation with them at lunch that one year, and suddenly when there’s a conversation about work, there’s a level of respect or a level of known truth coming from you to that person, because they had a previous conversation. You’re not just some unknown. It’s a very subtle difference, but just knowing who you’re talking to and having that conversation in the past has really helped me in a lot of cases.

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Mark: So what is your name?

Sheri: Sheri Bigelow.

Mark: And what do you do at Automattic?

Sheri: I am an Excellence Wrangler, so we do automated testing, manual testing, and keeping track of all the bugs for — I specifically work with a mobile division right now.

Mark: And how long have you been with Automattic?

Sheri: Going on 11 years.

Mark: That’s pretty close to the founding of the company, Sheri.

Sheri: It’s quite close. Closer than it is far. A lot actually.

Mark: So explain to me what your first Grand Meetup was like. Did you have a Grand Meetup when you started?

Sheri: No. When I started, we used to all meet up at WordCamp San Francisco.

Mark: Got it.

Sheri: I’m very extroverted, but I was so nervous, so nervous to meet new colleagues. I looked up to everyone so much and — one thing that I still laugh about and tell quite often — I told Matt, “I love everyone.” And he just kind of looked at me and he said, “You haven’t met everyone yet.” I said, “I love them all anyway.” I was so excited. It was a really fun time. 

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Ben: Thank you, Sheri. Hello everyone, Ben Huberman here. The Grand Meetup is a huge undertaking that takes years to plan. We’ve heard from people from all over the company talk about what it’s like to attend the GM. Now let’s talk to someone who knows what it takes to actually pull it all together and make it happen.

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Ben: Okay. Hello?

Megan: Hi.

Ben: Could you tell us your name and title please?

Megan: Megan Marcel and I am an Events Wrangler on the Events team at Automattic.

Ben: Could you tell us a little bit what an Events Wrangler does?

Megan: Sure, so Events at Automattic. An Events Wrangler ranges from sponsorships, to our internal meetups — and the biggest meetup being our Grand Meetup, which is when the entire company comes together for a week of team bonding and learning. Really the one time we’re all together in person.

Ben: When did you start getting involved with planning this event?

Megan: I got started working on the Grand Meetup when I first got here. I got off the plane at the Grand Meetup and I was helping people get on buses, but really sticking to it full time for the past two-and-a-half years, last year being the first that I completely owned the Grand Meetup. I’m leading.

Ben: I can imagine that people who’ve never been to a Grand Meetup might not have quite an idea of how complicated this process is. Maybe you can tell us a little bit about what this process entails. 

Megan: Right now I’m starting to plan for 2021 locations.

Ben: So two years from now.

Megan: Two years out. But the real planning begins about a year out. We’ll go to contracts, potentially earlier than that. And the real planning starts about six months out. That’s when we start doing it full time — all of the logistics, from people getting visas to come to the Grand Meetup, booking flights — and then we start getting to the stuff about when they are actually on site.

Ben: How many people work with you on this? Cause this is a huge undertaking.

Megan: It’s a huge undertaking and definitely not one I could ever do alone. We have two full-time folks that work with me on the Grand Meetup, and then our extended teams. So on site we have about 10 people dedicated to working on the Grand Meetup, and those folks will help a couple of weeks out and get them all ramped up for what’s to come on site. This way they can easily transition into the Grand Meetup once we’re here.

Ben: Right. Maybe one thing that we are curious to hear about is how you choose the locations. Right now we are in Orlando. 

Megan: So we want to choose a hotel that’s able to accommodate us ideally for two years in a row, because we try to go back to the same place two years. For people who attended before, it’s a little easier for them. And then us, coming to plan it — it’s a lot easier because we have those connections with the vendors that we’re working with. So everyone from the hotel to the AV team, to the transportation company and everything in between. Making sure that they can accommodate us two years in a row, that many people. And we’re also looking for a lot of meeting space. Also hotel rooms. We try to keep everyone at the same hotel — just really creating our own hotel. We actually have our logo on the building this year, on the hotel.

Ben: It looks great and I know many people who listen to this could not have seen it, but it looks pretty fantastic.

Megan: Yeah. So we just try to incorporate all of that and work with a hotel that understands we have a lot of different needs that we have to accommodate, with people coming from different cultures. We have different dietary [concerns], so we’re working with a chef that is willing to work with us to make sure everyone’s comfortable.

Ben: What are some of the most challenging aspects of planning the GM? I can imagine that, for example, working on the menus is one of them, because there are so many parameters to consider. Are there some other things that we might not expect but in real life are super challenging?

Megan: Yeah, for a couple of fun examples… My credit card has gotten declined many times —  when you try to order 600 yoga mats to do a breathwork session. Right before we were coming here we were dealing with a hurricane and an airline strike. So, trying to figure out how many people we could rebook on a flight for the very next week we have to…

Ben: Sorry to cut into it, but just to make sure that we know how many people are actually here. Right now.

Megan: We have 808 people here right now, not including speakers. We also wrangle all of our speakers, so all of the programming, researching speakers, then connecting with them, contracting them, getting them here, doing rehearsals with them, and we doubled the amount of external speakers we have this year for keynotes. So we have eight this year and that’s not including any of our workshop speakers who are coming in.

Ben: Do you have any favorite memories either from, I know this GM has only kind of started, but I don’t know from either this one or previous ones. Moments where things kind of clicked for you and you thought, “Oh this was all worth it. All my hard work has paid off.”

Megan: Yeah, just seeing people, the smiles on their faces, the small details. If someone’s birthday is this week, getting them a birthday cake, it makes a world of difference when they’re away from their families during this time. I would say being in a general session and having a speaker on stage where the audience is just completely connecting and the thank you’s and people just being so gracious. Everyone is really happy to be here, and just making those connections and seeing people make those connections is just incredible. You see it in the hallways, you see it everywhere. Also, just making the culture of Automattic come to the hotel wherever we are. It’s Automattic.

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Ben: This is Ben again. Everyone at Automattic has their own experience of distributed life. Some of us are constantly on the move. Others log into Slack from places like Tasmania or Uruguay or Nova Scotia. Some work from home, where they might also take care of family members or pets. Others, like me, mix it up a little between our home office, a favorite cafe, or a coworking space. One reason the Grand Meetup is special is that it gives us all a chance to learn from one another about what’s possible once you join a distributed company. We were able to capture a few of these stories, so let’s hear some of them.

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Will: So for the previous three years I was in a camper. I was on the back of a pickup truck and on the Pan-American Highway for the most part. There were some diversions into Brazil, into a lot of Argentina, a lot of Bolivia. 

Ben: How does that even work logistically? Can you just park somewhere, get internet, and then just do your work? How does it work in reality?

Will: You know, this is the age of the internet. Anything is possible. There are apps. And so we relied on an app called iOverlander. This is this crowdsourced app and it was people who lived the same lifestyle we lived. They would drop a pin on a map and they would leave a comment like, “This is a campground, it has WiFi, there’s hot water (or not), there’s electricity (or not),” or “What is the voltage?” So all of this data is all right there. And then you can spend a little bit of time extrapolating all of that data and putting it on a graph or a map or whatever. That’s how we lived, was mapping out the route based on connectivity.

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Sheri: I just joined a coworking space actually, and I don’t want to go there often, but I want to go there sometimes, so I can be in a different space and have a different experience and have some more working social time. I love-hate working from home because I’m extroverted. Love that I don’t have to do a commute. Hate that I don’t get to be around my colleagues more often. Not only that, remote. I hate that I can’t go and see friends that I’ve made at the company in the city where I live, or even several hours nearby, right? There’s friends from all over. So the Grand Meetup is really nice and really connecting, and it helps you work so much with people.

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Josepha: When I got here, everyone was like, “It’s great because you can work in your pajamas if you want to.” And for the first six months I did. I didn’t have a dedicated office area and I just sort of got up and started working whenever I felt like it, and finished working whenever I felt like it. And I found that that was not a good choice for me, especially in the work that I have to do. It ended up making me less resilient, more reactive, and also I had no concept of when work started and stopped. Our brains compartmentalize the information that we need in various places, and so when I lived and worked and did all of that stuff all in the same area, my brain was like, I guess we work all the time now, cause we work in our pajamas and we work on the sofa, which is also where we don’t work. And so this is just what we do. We work 24/7 I guess. It was a rough first year for me frankly. My first year here I really felt like Automattic and Matt had made the wrong decision in hiring me, because I was having so much trouble getting used to it. So now I have a dedicated office and I have my work computer, which does not come out of my office unless I have to write. If I write, I go to a different room that has a taller ceiling.

Mark: Explain that.

Josepha: I’m just going to tell you everything about how I have hacked my focus. So I have found that when I’m in a room with a shorter ceiling, I’m able to focus better. But if I have to do creative work, I have to go — or rather it is easier for me if I go to someplace with a higher ceiling, because it frees up, it just changes this idea of what I’m doing. It changes how I feel about it. And so interestingly enough, when I have to do really unpleasant writing work, which sometimes happens, I do that on airplanes, cause it’s a very constrained space, but I’m 30,000 feet in the air. I don’t have any place to go. I’m very focused, but I still I’m able to get that really creative, generative feeling so that I can get the writing done, because I’m flying through the sky on a tin bus.

Mark: So when you’ve got a tough email to write, you’ll just book a flight somewhere?

Josepha: Yes, I do all my emails on airplanes. No, no. If I have a tough email to write, generally for an email because it’s that short, I will just get up and walk into the high-ceilinged room and then walk back to my computer.

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Mark: That’s great. Now tell me, at home in your house, tell me about how you work at home, and where that is, and what your days look like.

Aaron: My day’s fairly structured in terms that — I get up in the morning, I put the coffee on and I change clothes. I don’t work in pajamas normally, so I have a ritual where I feel like I’m starting work. I’ll hop online and check out things that people have messaged me about overnight. My team is very geographically diverse, so when I come online in the morning, they’ve been working for several hours, if not longer. So I’m playing a little bit of catch up, but I also don’t let that be the focus of my morning. I figure out “Where am I most useful at this point in time?” Because within maybe an hour or two, some people may be going offline. So there’s very little chance for overlap with a lot of people on my team. About midday, it’s when I usually try to get outside. I have ADD, Attention Deficit Disorder, and did not realize that until I started at Automattic. So one of the founding things that I realized — in order for me to be successful, I need to do some sort of physical activity at some point during the day to help reset my brain. It feels like I’ve had a good night’s rest and it’s like another cup of coffee, if you will, but it sustains me for the rest of the day. Then I don’t feel like I’m trapped within the four walls of my office. So I’m also one of those weirdos that’s out at -10 degrees Fahrenheit in the winter, going for a run. Just because the feeling of being outdoors is really what recharges me, and then I come back and finish my workday. Sometimes I’ll split it up and get some tasks done during the light hours and then in the evening I might catch up a little bit on the things that were maybe less deep work. So, shallow work — things that maybe don’t need my full concentration.

Mark: One of the interesting things I’ve noticed is that Automattic has the ADDmatticians channel and neurodiversity channels for folks to swap tips. What are some things that have been shared among the group in terms of how distributed work works for neurodiversity and for how you work within that?

Aaron: I think the big takeaway is that like most people that belong to any type of unique group, if you have neurodiversity, it means a lot of things. It includes people on [the] autism scale or in my case, Attention Deficit Disorder. In my mind it’s a collection of things that you can’t see that affect a person to see or feel the world differently. So the biggest takeaway that I have, that I’ve shared with other people, is that you have to be responsive to your own signs of being overwhelmed. You have to — self-care is a really simple way of putting it, but you have to develop a mechanism to address when you are feeling overwhelmed. I’ve tried to lead my team with vulnerability, both from myself, and I try to encourage other people to be vulnerable. I think that’s what the ADDmatticians channel and being open about neurodiversity does, is that it establishes that we all have — I’m not going to call them faults — but we have unique things about ourselves that are different. You can only work better with people if you know what unique things make them different from yourself. In my case specifically with ADD, if I’m having a day where I can’t concentrate, it affects how I’m leading a meeting or how I’m having a broken conversation with someone because I’m doing several different things. Then I’ve asked people to call me out if they feel like I’m not giving them the focus that they need. So I’ve been very open with how my brain works and if I tell people, look, I need to go out and go for a run, my brain’s just not working. They know that I’m not just trying to get away from them. They just know that I’m trying to be in the right moment or in the right spot for them and it’s — I don’t know how I could do that without coming across as being non-committed to the team, without telling them with honesty about what is going on in my brain. So me leaving them to go for a run doesn’t mean that my running is more important than them. I’m actually doing this to help me be a better team lead and a better coworker.

Mark: It seems to me overall that distributed work is a huge positive for those that are differently-wired or operate different. Just in terms of — you’re in control of your surroundings in a much deeper way than having to go into an office. Is that your finding?

Aaron: It is, for those of us that are fortunate to have the ability to have a quiet space or to be able to model an office that supports their needs. I feel very fortunate that I’m in a place where I could buy a house that’s more suburb or more rural, and I don’t have a neighbor necessarily outside the window with a leaf blower during the middle of the day. I feel empowered to be able to change things, to make the environment as best as it can be. There’s no requirement for me to have a certain chair or certain desk, and granted, Automattic does give us the ability to buy a really great chair and a really great desk and have the computers that we need, so that eliminates that from being a concern, which is a huge deal for me. Having a great posture and having comfortable things to work on, that’s a majority of what I need. But not everybody else, from previous jobs I’ve worked in — places where the air conditioning didn’t work right. Or one person was fiddling with the thermostats. I have complete control over that. I can move the thermostat as much or as little as I want. Or if I’m having a day where I just want to go work outside, grab the laptop — as long as the WiFi reaches, I’m good to go. 

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Josepha: I’ve worked in high-stress environments my entire career, so being resilient no matter where you’re working has always been very important to me. And this is a particularly difficult thing, because when you work in a distributed fashion — and I work with the open-source community, so volunteers also — all three of the major risk factors for anyone working with employees come into play there. So you have to delegate things. And for volunteers you’re not delegating, you’re asking them to take part in that. So you are delegating things, which is this huge level of risk. You have all these people that are far away from you so you don’t see them every day, not only [do you not] see them physically every day, but so often we lose track of them because your DMs close so that there’s less noise, but then you forget to go and reach out, and so there’s that one. And then of course the third one, which is the fact that we work in a cross-cultural space, not only geographically cross-cultural, but for the community itself, for open-source WordPress, the different cultures of distributed work versus co-located work. Those are massively different cultures. And if you’re not aware of how that works versus this works, those two different entities, you never have any concept of how to invite yourself into the space in a way that that works for both sides. I spent a lot of time thinking about how to make sure that all of my teams are resilient because we do really hard work on behalf of the community and on behalf of Automattic in the community. And it’s important to me that they’re happy and healthy and safe for as long as they want to work here.

Mark: That’s great. Can I ask you about Slack real quick?

Josepha: Mm-hmm.

Mark: So do you have Slack on your phone?

Josepha: I do.

Mark: You talk about keeping your computer room and having a set specific time in which work and personal do not overlap as much. How do you deal with that, with your phone and managing your own phone time and asynchronous versus synchronous?

Josepha: I feel like Slack has become the new email. So there’s that. And I do have Slack on my phone. I am in about 15 different Slack channels — Slack instances on my computer, but only two on my phone. One that is Automattic and one that is the WordPress community, not in anything else. And that is specifically for emergency situations, or when I know I have to be moving, but I want to be able to be available for people. I am incredibly aggressive with my do-not-disturb time. It starts at 8:00 PM every night and turns off at 7:00 AM the next morning. And mostly it’s there in case I need it. And I have just convinced myself of that to be true. That’s the only way. A lot of times you just have to remind yourself constantly “this is not for me to be a slave to that information.” It’s in the event I have to get it. And so there’s that. But also I have themed days for what I work on, and also specific times of day where people can expect me to actively reach out and answer their questions. So at 10:00 AM and at 4:00 PM I will go through and respond to any open questions that people have given me over the course of the day or the evening. And I have themed days. So Wednesday, I always do my community check-ins. I check in all the team reps — well not all of them, as many team reps as I can get hold of. I check in with all of them all day on Wednesday. Thursday is a strategy day, so everybody comes into basically a very long meeting with me where they can drop in and out and discuss strategy problems that they have. And Fridays are when I follow up on everything that people need to be responding to me about that they’ve forgotten about. And then Monday is internal Automattic days. Tuesday is external blogger for the community days. I don’t know why I started with Wednesday and worked my way back around.

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Mark: So you have not only worked in this structure for a long time, but you’ve studied it and written about it for a long time. How would you say Automattic’s distributed work model has evolved while you’ve been here?

Erin: It’s super fascinating for me because I come from a background in consulting where I was actually helping enterprise companies to work better together. And one of the first things I understood coming here is that the way Automattic was organized, even at the smaller size it was, is that a lot of the practices inside Automattic at that small size were the same practices that I was trying to put in place for companies 1000, 10,000-people large. So I was like, “Oh, that’s interesting. They’re already doing all the good practices because working remotely forces them to.” So that was one of the very first insights I had because that also means that scaling that stops being a logistical issue, a tool issue, and you can focus all your efforts, instead of on the people on the leadership, on the processes. So all the things that instead are actually the problems between people that need to scale. And I think that’s one of the biggest advantages we had. And that hasn’t changed because we were 200 people. We were using certain tools. Yeah. The chart we were using at the time is not the same chart we use today, but it’s still the same kind of scope and tool. And we are now a thousand people roughly. And this structure in that sense is still the same.

Mark: Now given that you have studied this, written about it, consulted — what is Automattic doing right and wrong with distributed work? We must have some bad habits that exist, that maybe frustrate you.

Erin: Yes. So let’s start from this. What we’re doing right is, in terms of what is usually referred for example, as a flat organization — but we’re not flat. So the way I would define is that, there is no boundary in contacting anyone in the company. I should probably find a better, catchier way to say this, but we have a hierarchy, but the point is not the hierarchy. The point is that I can reach anyone in the company in any given time and, may actually encourage it to do that, if there is effectiveness. Again, you touched on a topic that is not really about the tools, right? It’s more about the culture and interaction between people. And I think that there’s a little bit of an obsession in the sense that, “Oh, the company’s failing because this information that I used to post, before everyone read it and suddenly I have a problem because I don’t know anymore where to post or where to discuss things.” But we grew, right? We are a larger company and we all know from, for example, social psychology, that we can hold in our mind roughly 200 people, 250 people, as our close connections. And of course it doesn’t limit work, but let’s assume for a second that 200 people is limited to work. Now if you’re a 200-people company, you pretty much know exactly where to send the right message to the right people. It’s natural, it’s implicit. You don’t even think twice. Where you are a 500, a 1000-people company, 10,000-people company, suddenly you’re like, “Oh, wait a minute, my information. How to propagate? How to make sure the right people listen to it?” This is not a problem solved with any tool. It just a matter of skill. Shaping the information channels is part of, in a way, the management, the leadership that should act as a filter. And this is one of the reasons why I’m not a huge fan of flat organizations because I believe that a structure — organization hierarchy works, if it’s a communication hierarchy. It doesn’t work if it’s a power hierarchy, but if it’s a communication hierarchy, it’s effective in helping convey this message.

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Mark: Hi everybody, Mark here again. Distributed work is a mode of doing work. But it also changes the ways we live our lives, and it expands the possibilities for work/life balance. Ben and I talked with some folks about what distributed work means to them, and some of the conversations that came out of that were pretty moving. Here’s Ben speaking with Will Brubaker to start us off. 

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Ben: What are some of the other challenges that being part of a distributed team like yours bring into the picture that you wouldn’t necessarily encounter if you’re all in the same office?

Will: Well, time zones is kind of obvious. When are people awake? This is also very important to “When can we have the best impact? Where are the people who use our product? What time of day are they asking for help? What time of day do they need our help? When do we need to be solving problems?” So we have to balance all of that out between our own needs because we do have our own lives, and we have people in our orbit — our spouses, our children, our parents, our friends, our — everybody. So we have to balance all of that.

Ben: Do you have any kind of system or tools that help you stop work when it’s done? Cause one of the challenges of being at a distributed team is that, if you work from home, for example, your home and your office are the same space.

Will: Boy, this is a… Yeah, your home and your office is the same space, and this is such an interesting thing. And also your question about how do you balance all of this. It becomes a question of “Do I work from home or do I live at work?” And that’s its own thing.

Ben: Is it still a work-in-progress for you or is it something you’ve figured out by now?

Will: You know, I’m very much in a transition mode right now myself in a lot of ways. And this is — part of the changes that have occurred as the company has grown over the last couple of years is that we have to be a little bit more rigid. We’re covering a lot more ground. Things are happening a lot more rapidly. We have to be able to react in a much more predictable way now. So I need to be able to say that, you know, next Tuesday I am working from this hour to this hour, and I need to commit to that. And so this has been a challenge to get there, but it’s also… I also get to decide that. So if I need to move all of my work hours until the afternoon so that I can do the things that I’m obligated to in the day, I can do that. When we were asked to start working weekends, I was a little bit resentful about that, and I had a very, very strong team lead who supported me, and we ended up working out a really brilliant solution where now I am working every Sunday and I am happy about it, where I was digging my heels in against working weekends. But we found a way to make this work to my benefit, to the company’s benefit and it’s a win-win situation, and this is the company that allows that to happen.

Ben: What are the benefits to being — you just mentioned a couple, but what are some other things that have made working for a distributed company better for you or for your life in general?

Will: To put it in the simplest of terms, I’m working for a company that allows me to be me, and I believe that to be true across the board. And I look at people who were in onesies as cartoon characters, and this is who they want to be. And everybody is really cool with that.

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Rocío: There is a map where you can see all the heads of Automatticians. I was the only one there in that super big island full of snow. Basically, my husband got an offer, a very interesting professional experience to work there. And it was scary at the beginning, but we said, “Hey, let’s take the chance, let’s have that adventure and let’s see how it is.” There is nothing to lose. So I was working remotely at that time already. And living there, it was when I joined Automattic, because for me it was clear. I want to work remotely to be able to live there. So for me, it was awesome. It felt like, “Wow, I can be here, in Greenland, in this extreme weather, right. And to be working for a company that I love and doing what I love without a problem. Wow, that’s a nice feeling.” If someone wants to try to work remotely, I will say “Try.” And don’t expect people to be behind your shoulder checking work you’re doing. Just be proactive on finding solutions, doing stuff, and asking for answers when you don’t know how to do something. When you’re working remotely it’s very, very important to communicate as much as possible with your colleagues because it’s the only way for you to say, “Hey, I’m here,” and to learn from them. If you are in the office and you are new and you don’t know things, you just turn your shoulder to the right and ask for questions to your colleague next to you. But we don’t have that when working remotely. So I will say if you don’t feel secure about things, just ask. Because in this company, everybody knows that communication is oxygen, and we really apply it. Ask for questions. People are going to be helpful and never, never feel ashamed of it.

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Mark: As you can hear, there’s so much more to distributed work than hanging out at home all day. Here at Automattic, we try to find solutions that make our work more effective and collaborative — but it also allows us to tailor our own work and environment based on how we’re wired. My colleague Aaron Douglas has some great insights on this… 

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Mark: Now, you wrote a blog post that made the rounds inside of Automattic. Which is basically, How Remote Work Saved my Life.

Aaron: Right? Yep. That’s it.

Mark: So tell me a little bit about that.

Aaron: About two months after I started Automattic, I was overwhelmed, and I knew that my brain works differently than a lot of people, in terms of my focus and attention. It was never really an issue because I had ways of handling that, and actually working in a regular office where you’re constantly being interrupted, being asked to come into meetings, or the person next to you starts having a conversation you’re listening in. It actually worked really well with how my brain’s wired, but then when I started working at home alone, it was really only my own mind defeating myself. So it was all on me to keep that train going during the day. I didn’t know how to cope with it though and so I talked to my physician to say, “Hey, I think I have ADD, I think I’ve had this all my life, but I’ve just never needed to worry about it.” So that sent me on a path of talking with a counselor, [to] start developing a tool box of things to help combat the issues I was having with focus.

The frustration was pretty real and I needed to walk away from my computer one day and it was, I literally walked outside, took a short walk, which is something that normally I’ve been doing. In a regular office, you go for a walk during lunch and you come back all sweaty and you’re worrying about smelling and not every place has a great shower room. It just was an excuse for me not to do something more physical during the day. But at home, who am I trying to impress? As long as I look presentable for a webcam, I can wait till midday to take a shower if I want to go for a walk. But what I realized early on is that, when I came back from those walks, my brain felt almost reset for the rest of the day, and that turned into a daily habit over time. There’s a lot of bits of story in between, but essentially, I went from the occasional walk, to riding my bike, and then to doing running as well, and it’s now a daily habit. I feel strange when I don’t have the ability to get outside and do that exercise, and it’s part of my toolbox.

Before I started at Automattic, I was having issues with atrial fibrillation, and that is where the electrical system — your heart just goes wonky and it doesn’t beat right. The major issue with that is it can induce strokes, because when your heart’s in a stopped pattern, and the blood’s in an area where it shouldn’t be, it can pool and form a clot and that can go into your brain. So I was really scared when I heard that. So that combined with needing to be outside, to help reset the brain, which is like a one-two punch to motivate me. My focus this entire time has just been on my focus. The side effect is that I’m actually, I’m over a hundred pounds lighter than I was before starting at Automattic. I feel like even though I’ve aged, I feel like I’m healthier and I feel younger than I have, and I attribute a lot of that to Automattic and working remote, my coworkers for helping encourage me, and finding friends to just socially run with them, like Strava, Runkeeper, one of those services. That’s been a big part of what’s kept me going and now I’m returning the favor, and also helping other people motivate themselves. So yeah, that’s effectively how I think Automattic helped me save my life. Because I’ve gone from being dependent on medication for atrial fibrillation and feeling defeated, to feeling fairly successful with my attention problems and being off of the medication for my heart, and overall just being in a healthier place.

Matt: Hey everybody. Matt Mullenweg here again. As Automattic has grown, so has the number of perspectives on the freedom, flexibility, and occasional challenges that come with distributed work. It’s really amazing and humbling to listen to these stories, and to be able to relive the magic of the Grand Meetup too. Thanks to everyone who shared, and to Mark Armstrong and Ben Huberman for capturing these powerful stories.

As you’ve heard, hosting the Grand Meetup every year takes a lot of work. Booking hundreds of flights and hotel rooms, the food, the speakers…it’s a lot! But we think the value of the connections that people forge with their coworkers vastly outweighs the cost, which is now getting into the millions of dollars. This meetup, and the smaller ones that our individual teams have throughout the year, are vital for a distributed company.

On the next episode of the Distributed podcast, I’m going to catch up with an old acquaintance of mine, Anil Dash. Anil is a pioneer who really helped define what blogging looked like back in the early aughts. He cares a lot about the Web and about technology, the direction both are going, and how they affect everyone. 

Anil runs a semi-distributed company called Glitch, which has developed a social platform for building and sharing apps. The team at Glitch puts lots of thought into creating a work environment that centers employees’ wellbeing. I’m interested to learn how the company’s decision to go distributed fits into their commitment to employee care. They have an office in New York, as well as being distributed, which is also very interesting to me, now having an office in New York at Tumblr. 

Thanks so much for listening and see you next time.

Read more about Clark Valberg in “Building the Tools that Bring the Screen to Life.”

InVision CEO Clark Valberg needed a tool to help his distributed team collaborate on design projects. So he created it — and it became the company’s flagship product, one that every Fortune 100 company now uses. In this episode, Clark joins our host Matt Mullenweg to discuss how he built his distributed company, and how that structure informs InVision’s collaborative-design products.

The full episode transcript is below.

***

MATT MULLENWEG: Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg. 

My guest this week is Clark Valberg, the founder and CEO of InVision, a company that makes a collaborative design platform that’s very popular with distributed teams. It does ideation, design, prototyping, sharing… and it all lives in the cloud. No more emailing files back and forth — it’s pretty slick. 

Clark founded the company seven years ago in Brooklyn, and now they have over 5 million users at places like Airbnb, Amazon, Netflix, Starbucks, and my company, Automattic.

Like Automattic, InVision is fully distributed. And they’re similar to us in size, so I’m interested to hear from Clark about his experience leading and growing a distributed workforce. 

Alrighty. Let’s get started.

MATT MULLENWEG: Welcome, Clark.

CLARK VALBERG: Hey, great to be here.

MATT: Y’all are one of the other big fully distributed companies. Tell me a little bit first about what InVision does for people in a cave who might not know yet. And tell me a little bit about the scale of what y’all are doing in the —

CLARK: That was my opening to you, by the way. Oh y’all are one of the other largest remote companies. This is a constant debate, by the way, internally, which one is bigger.

CLARK: Okay so Clark is the CEO and Founder of a company called InVision. InVision is a design collaboration platform. Most of the products — I hope most of the products — that you use everyday, if they’re well designed, if you love them, if you feel excited about how they work and how they fit into your life, it’s because the design of the product is good. And so that’s where InVision comes in. We are the place where those products are designed, tested. We’re the stakeholders that make that product great, are engaged, we are both the design tool and the place.

MATT: So if you were to describe what it’s like to use an InVision product. Let’s say I’m a designer, I’m collaborating with another designer, what will we do?

CLARK: If you are a digital product designer, you need a place to design, you need the place to actually create the screens that make your product beautiful. That’s InVision.

MATT: So before, I would do this in Photoshop on my computer and now it’s happening in a web app?

CLARK: Photoshop or a cave wall, depending on how old school you are. So yes, you would’ve done that there and now you do that [in] InVision and then InVision is also the place where that design comes to life in a collaborative sense. It’s the place where you put your design so that others can look at it, engage with it, give you feedback on it.

The question you’re asking is fundamental to this transition of design altogether, which I can talk about for a long time, but design is no longer a job to be done, it’s now an organizational discipline in a world where the screen has become the most important place, or one of the most important places in the world.

MATT: When and how did design become important to you?

CLARK: I ran an agency and dealt with what was the general operating dynamic of agencies at that time, and probably still today in many respects. You have a client, they have an idea of what they want, they have some business problem they’re trying to solve and you’re trying to put together some kind of a requirements document, some kind of a contract that hopes to look into the future and imagine everything they’ll ever need to accomplish whatever business goal they’re trying to accomplish, and define that today, or at least in the next few hours until we can get this thing signed and move forward.

So this idea of up-front definition bothered me, that was a deep intellectual itch. How can I, instead of creating a contract that separates me from the client and hopefully mitigates the legal risk of giving them exactly what I told them that I would give them, and we’re charging by the hour, how could I align my values and go on this journey with them together side by side? How could I act as their guide toward the business reality that we would ultimately end up discovering together?

Any time there’s a client, there’s that dynamic of — you know what you want in your head; it’s impossible for me to get that out of your head and get it into my head. And by the way, even if I could, hopefully if we do something right that will change over time, the more articulate that vision of the future becomes.

MATT: How did this agency look? Clients, were you meeting them in person, were your colleagues in person?

CLARK: Both. It was my first dip of toes into the world of being able to work with people seamlessly online. So a lot of the fundamental inventions, collaborative inventions that we have here at InVision — 900 people, totally remote — came from that world of just trying to make clients happy at a much smaller scale, sometimes remote.

MATT: How big did the agency get before you switched to doing the product work as your primary thing?

CLARK: The biggest ever? I think it got to 25 tops. So it was a small agency. The word “boutique” sounds much better than small, doesn’t it?

MATT: There’s probably a lot of people [who are] part of or running agencies, listening to this [who have] that dream of switching to be a product company. What advice do you have for them? What made it work for you? Because there’s so many examples of that not working.

CLARK: I’ll tell you, I did not have a vision of becoming a product company. It happened as an extension to the reason why we started this agency in the first place. So the agency was founded on, “Hey, instead of ending up in these weird litigious, semi-adversarial relationships with clients, what if we could figure out a different operating model, a different communication model?”

So we started by building prototypes, and we would write those prototypes in code, we would show them to clients early, we’d be able to have a diverse conversation across the organization, instead of just dealing with one project manager, we’d be able to embrace all the different business leaders that represented the parts of the business that we were trying to serve with the software. We’d have holistic, multi-dimensional, diverse conversations. That was the whole idea.

I wanted to be an agency that loves its clients. I want to be on the same side of the table. These were all the different key words, [laughs] the key phrases that we used to make ourselves sound different and differentiate. But I think it sprung from a place of what we saw wrong with the industry. And then that tool called a prototype just evolved over time.  

And at some point someone — not me — said “Hey, what if we just took designs out of Photoshop and connected them together and turned them into a little simulation that was almost as high-fidelity as the coded prototypes that you were building? It would be almost good enough and probably you could — we’ll just run it as an experiment but it’ll take an eighth of the time to build and maybe we can use that as a communication device.”

MATT: Who was the first client you tried that on?

CLARK: It was a company in upstate New York. So this is one of our few fully, fully remote engagements, like we went to see them maybe once a quarter but other than that everything was happening online. I’ll reserve the name but a large education-product company. They created educational products that they sold into school districts. And we were building essentially a totally custom ERP solution for them — every part of their entire business modeled into a piece of software, every experience that exists between two people in that entire company was modeled into a screen some place.

MATT: Wow.

CLARK: So a very sophisticated piece of software. And it would have been an absolute nightmare had we not employed this process because there were just too many stakeholders with too great a diversity of perspective on what needed to be built, and it just had to be a conversation that happened over time. This was a “Let’s try this new thing. What do we call this new thing?” I think literally the time that we’ve been on this call so far was the time it took us to come up with the name InVision. [laughter] I think it was the second idea, like, “Oh, we’ll just change it later, that’s fine.”

And we had absolutely no interest, almost an explicit disinterest, in having anyone outside of the company know what this thing was. This was just for internal use only. Somebody even said “Hey, what if we wrote a blog post about this? What if we..?” And once it worked, once we saw that it would totally change the game for us, and it really did in very profound ways, this is like a whole new movement for agencies, this would be a cool thing to talk about. I said, “Absolutely not. This is our differentiator, this is our competitive advantage in this agency, maybe let’s just keep this under hat.”

MATT: Ha!

CLARK: Luckily someone — it’s good to have a lot of people who disagree with you all the time around you, otherwise you end up being a victim of your own vision.

MATT: So at this time, it sounds like you have an office and colleagues in that office. At what point did you switch to being fully remote and using these tools to enable that?

CLARK: Even the agency was hybrid. And in New York City, my entire movement into a fully remote world — again, never had a vision for it, didn’t think this was the future. I’m still not sure if it’s the future for everyone, okay, this is a matter of significant debate and worthy of debate. It was a necessity thing. So the agency was a hybrid but let’s call it a reluctant hybrid, like “Hey, we can’t find enough people in New York so we’ll hire people who aren’t here and we’ll just deal with the overhead and managing that overhead, that collaborative overhead as a cost of doing business.”

When we transitioned into InVision, so yada, yada, yada — we’re yada yada yada-ing through the birth of an entire company — but this product is cool, what if other people liked it? Let’s put it in front of the world and see if they bite. They did. We raised some capital and then we had to transition out of the agency and into the product company. I sold the agency to a — basically a hostile takeover. I sold it to my wife for a dollar. Literally, it’s a whole big story where the company, InVision, sort of launched its for-pay model on my wedding day.

So here we are with $1.1 million and an office that my co-founder and I are sitting back-to-back in a tiny Regus space in midtown Manhattan. I think it was the year that Google opened up the Google megaplex — I don’t know if it has an official name, but the building in Chelsea?

MATT: Yes.

CLARK: We just found that every conversation we were having with an engineer, designer, anybody, everyone — they were also talking to Google, they were also talking to Yahoo and Facebook. Anybody with a New York office with a more fashionable name and better ping-pong tables to our no-ping-pong tables was just destroying us for talent, and I found that we were spending all of our time wining and dining engineers we weren’t hiring.

MATT: Wow.

CLARK: And so we got together after about three weeks of slogging through this talent thicket, and asked ourselves an existential question. We did what we called a pre-postmortem — I’m sure you’ve heard this idea. Let’s look into the future, let’s imagine the things that don’t work out and let’s guess, based on what we know today, what are the likely sources of that failure?

And the biggest one for me was not spending enough time on the things that really make a business successful. At the end of the day, product-market fit is where it’s at, at this critical birthing stage. We have to get a group of people vehemently, maybe violently excited about this new product and talking about it to people. It has to have independent lift, it has to have word of mouth, groundswell. And what will we probably be doing instead of focusing on the design of the product, the marketing of the product? We’ll probably be trying to hire engineers and moving way too slow.

And we just opened up the envelope. And again, it may not have been me, somebody thought, “What if we just hired the people that we had worked with as contractors in the agency?” We had a pretty significant bench of folks that we pulled in who were full-time other places and just did little side jobs for us in exotic, far-flung destinations like Phoenix, Arizona… Houston, Texas. Places that were secondary, tertiary tech markets, folks that we just knew, knew from conferences, because they were developers in the same language that we were developers in — what if we just hired them full time?

So we said, what if we just did this at scale? What if we somehow figured out how to make collaboration work where everyone was remote? And I had a piece of advice. I don’t know if he even knows that he gave me this advice and how pivotal it was for me. Do you know David Cancel from Drift? I called him up. He had just sold a company to HubSpot. I ran the idea by him, like, “Hey, what do you think about this remote idea? What do you think about this talent hack — instead of hiring people in New York, we’ll hire them anywhere. We’ll actually pay them above market.” That was our thesis originally, to pay them above their local market but arguably below the New York market.  And there is a very, very wide spread there, at least there was then even more so than it is today.

And then sell them on this lifestyle change. Sell them on getting rid of their commute, sell them on work/life integration. This is the time where everybody talked about — the common theme was work/life separation — how do I turn off my phone, how do I turn off my email at a certain time a day?

We said, well, the people that we work with, they were moonlighting for us while working full time, they clearly have more passion, more interest in being involved in the work they do than 9-5, so maybe it’s not about a certain time of the day where you just die from work. Maybe it’s about having more control over when and how. Maybe there’s a work/life integration idea that we can start selling people that may actually be more meaningful than that separation.

And he liked the idea but he gave me a piece of very firm advice that we still follow today, which, you’re not following, by the way. I just want to throw this out there. It’s don’t go half in/half out on this. There has to be a sense that everyone has equal access to the executive team, to each other. And the way he put it, which I thought was a beautiful way to encapsulate it — there can’t be a place where someone is not. Your office, whether if they work in marketing, it’s the head of marketing. Everyone has to feel equal proximity.

MATT: And that avoids a classic problem, right, why I actually don’t like the term remote, that some people are more like second class citizens in the —

CLARK: 100%. You have a room and then there’s that guy on the wall who’s trying to get a word in edgewise. I said, “Well how far do we go with that? Can we have some kind of a New York office?” He said, “I would say not.” And I think the next week my partner and I decided to disband the office, to shut down the office and to actually go home and work.

Even though we had been commuting into the city — I live in Brooklyn and he lived in Manhattan, he was a few blocks away from the office — even though we had been commuting and spending time together in person, and you’d think, “Oh the founding team, they have to get together and they have to collaborate, move at warp speed and problem solving and collaboration.” I said, “I think we should discipline ourselves to be able to make this remote thing work even between us, and if we can figure that out, then that will scale to everyone else.” Big decision. Bold. I would say it was an absurd decision in some respects. [laughs]

MATT: I would call it radical actually, yeah, especially for the time. Because what year was this?

CLARK: Eight, nine years ago now.

MATT: Yeah.

CLARK: The only company that promoted itself as remote or promoted the idea of being remote or distributed was 37 Signals. And so they were the original inspiration for this or at least inspired us to believe it was possible.

MATT: Totally.

CLARK: So we did it, said “Hey, this is a design problem essentially, like many things in life. We’ll just design the people, practices, and platforms of the business.” We think about these three Ps all the time to establish a healthy rhythm of connection. And by the way, Joel Spolsky, another — I’m just calling out all the inspirations for this because it definitely didn’t come for me — wrote a book called “Joel On Software,” which I’m sure you’ve read, everyone has read.

MATT: Classic. I highly recommend it actually.

CLARK: Classic. He was a proponent of this idea of having an office with a door that closes. Now we think about it as deep work. This is a common theme that’s used in tech today. And I had this thought — I’m still not sure how valid it is — but that the percentage of intellectual focus — deep work — that happens in your business is a significant driver or limiter of the success of that business, to some degree.

If you have a large group of people who are really talented and have a lot of time to focus on the work they do well, and there’s an environment that brings them together when they need to be, but that ebb and flow of focus time, that intimate craft time and that kinetic energy of collaboration, but not at the same time. There is a dual-modality model that one can leverage to get the best out of both.

MATT: What percentage do you target for yourself there, and what percentage would you target for an individual contributor with a vision?

CLARK: The more creative your work, the more focus you need to move through the work that you do. I think real creative work is done alone. You know when you need to collaborate, you know when you need that validation from a third party, or your rate of innovation starts to slow to a certain point where you need to start sparking and stoking those flames of creativity through communication with other people. You have to build a system that makes that reliably happen at least at some point for each person on the team.

So early days, we had a stand-up, every team in the company. At that time we had three teams and 15 people. Every team had a stand-up. That stand-up had a ritual. It happened at the exact same time every single day. So 1:00, whole company, three or four questions. I think it evolved from three to four questions for each person, round robin. Obviously that’s much more difficult to pull off at 900, but that is scaled in different ways. Let’s make sure that everyone knows or is aware of the work that everyone else is doing.

That’s the fundamental platform that creates that connection. And then people go off and they do their own work as individuals or as groups, and they reconvene regularly to check back in.

MATT: So if I were an ideal designer or developer at InVision in this model, would I be spending 80-90% of my time in this deep work?

CLARK: I would imagine probably 70. I think probably people at InVision would tell you that they get less than that because there are many meetings, and at scale, obviously there’s an overhead, a connective tissue overhead to managing very large projects at scale that are cut across multiple departments and disciplines. Again, there’s no perfect formula, it’s just making sure that people can preserve that time, or as much of that time as they can.

MATT: I have a selfish question, which is, as a CEO of a distributed company, what do you think your percentage is of that work?

CLARK: Mine is probably closer to 30%. I’m not a production person. I don’t have a work product necessarily that I put into the world. I don’t have a screen that needs to be designed to an excruciating level of detail and iterated on over time.

MATT: I would say at this moment I’m probably under 10%. So that’s something I’m working on increasing because I feel like the time I’m able to invest in writing helps a lot, and the company is, of course, a product I think about a ton, and need to spend more time than I currently am investing in how that product is designed — the product of Automattic itself.

CLARK: Here’s a little weird hack. I don’t know if this makes any sense for folks. I like to sometimes just go to conferences, even though I’m 50% interested in the content, just because being at a conference blocks off your schedule, it puts you in a room with a lot of that kinetic energy, of buzz, of people who aren’t distracting you because they don’t have any interest in you, they’re there for other things, they have no connection to you, but it’s a room that’s vibrant with the energy of people. And there is someone talking and there’s time in between. And I find that just disconnecting and absorbing ideas on drip ambiently gives me a ton of headspace to have divergent thinking time.

MATT: That’s a cool hack. Now we opened a lot of threads there. I’m going to loop back to some of them. One, if you were doing a pre-postmortem today for InVision, what would be on your list?

CLARK: Oh without a question it’s the cohesion of the company. I mean it’s a risk being a remote company. There are things that happen in a co-located environment — that’s what we call the world of on-site work, co-located — there are things that happen there between the seams that people don’t even understand are happening. They don’t consider it an explicit part of the work.

A loose example — the watercooler. There is this — I’m bumping into people in the kitchen, in the hall. There’s this ambient transfer of energy through “Hey, you’re working on this? Hey what are you up to?” We have to figure out how to allow that to happen deliberately. If what we’re doing now is 80% as good as being in-person in some ways and 130% better than being in-person in other ways, how do we make sure that we take that 80 and get it to 100 so that we’re not leaving a liability on the table?

MATT: I’m particularly curious about that watercooler. What did you figure out and what has worked well so far?

CLARK: What I have learned in these settings is driving to solutions in real time. Again, going back to that ebb and flow of together time and alone time, it doesn’t work in larger groups of people. You can seed things, you can create good traction around the idea, but I think a longer, more thoughtful, more deep-work-enabled process of driving to a solution is important.

Where we are beginning to think about this is making sure that the time that we have together as an executive team, even the online time — two hours every two weeks we have something called the Strategic Alignment Team Meeting — so that group of people meets online, just putting more ceremony on that. So rather than getting together and just having a random group listing of things that we want to get through, maybe doing a little bit more pre-work.

So one idea that surfaced was taking a facilitator that wasn’t a part of the group — the Head of Biz Ops or Chief of Staff — and making that person responsible for interviewing all the members of that team individually, one on one, with a set of pre-defined prompts to pull out the value and get that value on the agenda ahead of time.

Because if I pulled you into a meeting, Matt, right after this call — I don’t know if you have a meeting right after our little podcast here, but if you did. you probably would not be in a state to pull out the most important thing that’s going on in the business or the biggest threat or the biggest opportunity or some weird HR thing, or opportunity or great idea that you thought about two weeks ago. You wouldn’t be in a state to evoke that unless you’re just a — you meditate a lot more than I do. I don’t know.

There has to be a mechanism, I think, for tilling that soil with those executives ahead of time, or with anybody in that case, ahead of time. So how do we create a list of questions? For example, what’s the biggest threat to the timelines that you’re facing, what’s the biggest HR or people or resource or talent issue that you’re facing? I’m just making up examples of kinds of questions we would ask. What’s the thing that you need the most from who on this team? I’m imagining a world where there are about five or six questions that we ask each executive one-on-one before getting into that meeting and that those questions ultimately end up tilling the soil and driving the agenda of the meeting.

MATT: One thing that I’ve heard that’s unique about InVision that I’d love to confirm is that y’all have everyone on East Coast office hours?

CLARK: I do believe that you need a certain number of hours of overlap. So we have a kind of a loosely held standard set of operating hours. I think it’s like 10AM to 6PM. The recommendation that is fairly closely held is that there should be a three hour overlap between most of the team because within those three hours you can negotiate when your stand-up meeting is. If you’re a team that works together, you can get to the wide-wide meetings, generally speaking, unless some people in Australia watch those the next day or a week later. I don’t know what the time is in Australia right now but you get the idea. Generally try to aim for three hours of overlap.

MATT: So does that mean you don’t have many people in the Asia Pacific region?

CLARK: I would say not by design. We probably lean out of hiring one-off individuals. We’ve done acquisitions, for example in Australia. We do have people in Asia Pacific for sure, but there is probably a light bias towards folks that fit into teams that have a schedule with more overlap.

MATT: The number I heard for you all, and this is the other day, is around 20 or 25 countries that you’re in?

CLARK: It’s got to be. Yes. I mean 900 people? Yes, probably 25 countries I would imagine.

MATT: We’re at a very similar size, I think we’re at 68 countries. I would say there’s definitely a cost and a tradeoff to having that kind of time zone overlap as an explicit part of the hiring, and it definitely means that there are certain teams that are more Asia-Pacific-centric, because that overlap is important. And if you have a single team with people in what I think are the three zones, South America, Europe, Africa, and then Asia Pacific, there is no good time for anybody.

CLARK: 100%. You have to be getting something out of the remote thing. It’s an interesting question. When people ask about remote, they assume that I’m a remote zealot. I’m not. I’m not someone who believes in remote as “this is the future.” I’m just not religious about the topic at all.

What we needed out of remote very early on is we needed it as a talent hack, as a talent arbitrage. Hire the best people wherever they happen to be, figure everything out later, hire them quickly, get them in the ship as early as possible and start seeing results. How can I just hire the best people no matter where they are? If you’re not hiring, if you don’t find that your talent density is significantly greater than your contemporaries that are co-located in whatever city you happen to be in, then you’re not leveraging that arbitrage the right way.

MATT: That’s a really good way to put it. How long do you think that talent arbitrage exists? Stripe famously now has remote as their new office engineering center?

CLARK: Sure.

MATT: How long before Google, Facebook, etcetera, the same people you’re competing with in New York, open into the distributed world?

CLARK: That time is probably now. It just means you have to be more creative. Also, even if ten of the biggest tech companies in the world were out hiring, the talent supply is big enough for us all.

MATT: Playing off on site versus off site, we have talked a lot about how you work in a distributed fashion. How and when do you bring people together?

CLARK: We have a company all-hands on site, a global all-hands, called IRL, InVision in Real Life.

MATT: Ha! I like that.

CLARK: This year it was in Phoenix, Arizona. We took over an entire resort and that was an intense, amazing, high-energy experience that brought a lot into the work that we do, that we have done since. And the year before that — also really incredible — in Los Angeles. I definitely like the format of all of us together in one resort better than all of us split up between a few hotels. So all company, all hands, IRL.

And then we have miniature IRL. So the product department has a product managers’ IRL, which I think was two weeks ago in New Jersey. And I think this week, if I’m not mistaken, is the all-designers’ IRL in Chicago. They pick a city that just makes sense. And I think there was CFT, the Customer Facing Team, was in Denver a couple of weeks ago. So departments have an IRL, the whole company has an IRL, and then individual teams can tap into budget to get together in person.

MATT: If I joined InVision, how many weeks or days out of the year am I going to be at these IRLs?

CLARK: My guess is probably three throughout the year. We also encourage folks to go to the InVision events that we have, the customer-facing events. Design + Drinks, we do panels, not a week goes by that there isn’t some sort of InVision customer event happening at some bar someplace in the world.

MATT: That’s really cool.

CLARK: And so we try to encourage some folks to get together that way. Again, this is personal, my personal principle behind this online universe is it’s called Cloud Culture — that’s what we call it — Cloud Culture versus the IRL stuff, when you’re in real life I prefer us not to be doing work.

MATT: Interesting.

CLARK: I prefer us to be connecting as people. If you gave me a week with the team together in person I would really like 80% of that to be stuff — it could be conversations that sound like work but conversations that really bring us closer together as people. My mental model here is that we have little scale models of ourselves. Even if we’re in person, we’re not really relating to the person we’re looking at, we’re relating to our little mental model of that person that rests in our mind. Does that make sense?

MATT: Sure.

CLARK: The more time that we spend together, the more articulate, the more detailed that mental model of you becomes. So when we’re online you get to a certain level of precision, [I can] take a long time to get to know you as a person and get to know how you behave and act in different contexts, how you react to certain things as individuals or as groups. When we get together, the fidelity of that model increases exponentially. And we take that mental model into the online environment. That’s the reason for the on-site, in-person experiences.

MATT: I’ve heard — you talk about the screen a lot but I have also heard that InVision — rumor — that you’ve banned slide decks.

CLARK: It makes a great headline, doesn’t it? [laughs] It’s not exactly true. What I’ll tell you is that we encourage visual collaborative communication in meetings more than prepared slides, only because that visual communication tends, number one, to be much more democratize-able. You can get more folks who are of a greater diversity of connection to the problem space.

If you’re going to present something to a product team, that’s one kind of collaboration but arguably a lot of those product conversations should reach far beyond the engineering, product, or designers who work on it. You’d like to be able to engage business stakeholders, domain experts that exist within the business, or folks that are impactful. You’d like to have your Head of Finance on a product call and to have them totally track an influence.

So staying visual, being sure that you just have a strong bias to visual communication, visual storytelling, getting visually-driven artifacts that are real to the customer, real and true to the customer experience, I think are really important. You generate better conversations than you would with a deck. It happens to be that we’re all trained when we see a deck. It’s like a movie, like “Now is our time to take out the popcorn, kick back and let someone else do the talking.”

When you do a Freehand sketch — we have a product called Freehand, which is basically a gigantic, online white board — or you’re actually showing screens of an experience, and tying the conversation around pricing into the user experience, that drives that conversation around pricing to the customer — two things. Number one, you’re being super customer-centric, you’re orienting all of the people on the call around the front line of that problem space.

Pricing is not a number conversation. Pricing has financial impact, pricing needs to be within financial guardrails, but ultimately pricing is not about a number, it’s about a customer experience. All of the leverage you have around pricing, all of the acceptance from the market that is required to make that price the right price — and now I’m spinning off into a pricing conversation, but you’ll understand how this is a microcosm for all these things —

MATT: Totally.

CLARK: — comes down to somebody looking at a screen at some point and feeling good or bad about it. So if you can have that pricing conversation through a lens of design — and by the way, this is what InVision principle number seven is meant to imply — being design-driven. How do we get into the mind and the heart of the customer and have the business conversation while we’re having the customer conversation?

Design conversation and business strategy conversation, all in one. If you can do that, you can have a much greater diversity of people in the conversation, your Head of Finance doesn’t feel like they’re on a product call, the product people don’t feel like they’re in a finance call, everyone feels like they’re in a creative problem-solving call.

MATT: I love it. Thanks again.

CLARK: Pleasure.

MATT: That was Clark Valberg. You can find him on Twitter at @clarkvalberg. That’s “Clark,” then “Valberg” — V-A-L-B-E-R-G. 

We’ve got a special treat in store for the next episode. Back in September, Automattic held its annual Grand Meetup in Orlando. The Grand Meetup is a time for all Automatticians to get together in one place. We get to meet some of our colleagues face-to-face for the first time, hear some great talks from folks like Stephen Wolfram (who was a guest on this podcast a few weeks back), and of course hang out and have fun together too.

We set up a recording booth at the meetup and talked to a bunch of folks from across the company to hear about their experiences with distributed work and the importance of in-person meetups for keeping people connected throughout the year.

Thanks for joining us and see you next time.

Read more about Lydia X.Z. Brown in “Making Work Accessible, Wherever it Happens.”

Because of their background in working with disabled and marginalized people, attorney and activist Lydia X. Z. Brown has a deep understanding of how different workplace environments can best serve diverse workforces. Today they join our host Matt Mullenweg to discuss what distributed companies can do to make workflows and working conditions more inclusive.

The full episode transcript is below.

***

MATT MULLENWEG: Howdy howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg. 

Today’s guest is Lydia X. Z. Brown, who is a… well, Lydia wears many, many hats — we’ll get to that in a minute. Lydia once gave a talk for Automattic about disability inclusion, and today we’re going to continue that conversation. 

Lydia spent much of their life feeling left out, and they’ve dedicated their career to advocating for marginalized folks of all kinds. As the CEO of a distributed company, I’m curious to know more about how we can make the hundreds of Automatticians across the world more comfortable at work, and I know Lydia will have some insightful thoughts to share about that.  

Okay. Let’s get started.

MATT MULLENWEG: Hey Lydia.

LYDIA X. Z. BROWN: Hi Matt. Thank you so much for having me on your podcast.

MATT: You are a multi-hyphenate. It says here you’re a writer-advocate-organizer-strategist-educator-speaker and attorney. How did all those things come to be for you?

LYDIA: I have believed from a very young age that every single one of us has a moral obligation to use whatever resources we have — time, money, knowledge, skills, emotional energy, access to physical resources — however that might be defined — that we each have a moral obligation to use those resources in service of justice, and fighting against injustice and oppression and violence in all of its forms, structural and individual, subtle and overt.

And since the time I was young, in grade school up through high school and now as an adult, I have done that. And I have been enormously privileged in many ways, although I frequently talk about experiencing marginalization in others, I have an enormous amount of privilege and I have experienced some of that in terms of access to some resources. And for me that makes the journey quite natural and quite intuitive. It wasn’t so much that I chose “I’m going to be this thing, I’m going to be an advocate, I’m going to be an educator,” so much as I have to. I have an obligation to, and I have the skills necessary to develop, so that I can be successful in doing it.

MATT: There is so much injustice in the world. How did you pick the areas that you focus on?

LYDIA: The work that I do is deeply personal to me. I am a multiply-disabled person. Most people who know about my work primarily know me from the autistic community. And not only am I autistic but I also live with psychosocial disabilities and other cognitive disabilities. And not only do I move through the world as a disabled, neurodivergent person, but I also move through the world as a queer person and as an openly non-binary trans person, and as an East Asian person of color living in the U.S.

And all of those experiences of marginalization, and what some of us might say is hyper-marginalization, people who live at the margins of the margins where there is so much that is stacked against us, and how society is designed, and who society assumes is normal and healthy and the ideal, and who society decides shouldn’t really be at the center, shouldn’t be in the lead, should be denied opportunities, should not have access and all of those things, it gives you a very different perspective than when you grow up in the world with access to more privilege and resources in ways that I didn’t, even in the many ways that I have had some privileges.

And for me, going through school, targeted all the time as a freak — that was one of the most common refrains of my grade school and middle school bullies — and making it to high school, where I was falsely accused of planning a school shooting because of stereotypes and stigma about people like me.

MATT: Oh wow.

LYDIA: And then making it through college and law school, where you would think that people might have a more egalitarian approach. Well, that’s laughable because sometimes the people that are in what are supposed to be the most progressive kind of spaces — forward-thinking, innovative — sometimes were the most damaging and the most harmful precisely because they already believed that they were incapable of inflicting such harm.

And moving through those spaces, constantly receiving the message that I didn’t belong, and at the same time that I couldn’t speak for or alongside or even in support of other hyper-marginalized communities, because, well you do have this privilege — it gives you a fire.

MATT: How do you develop empathy for someone whose lived experience is different from your own?

LYDIA: For me it starts with recognizing firstly our shared humanity and secondly believing deeply in and being passionate about a commitment to valuing all people and all configurations of people’s lives and experiences, and how their bodies and minds work, whether they are like mine or unlike mine.

And if we all start at that premise, that every single human is valuable for who they are in all of their complexities, in their many identities and experiences, not in spite of them, because we are not the same and that’s a good and okay thing, but as all of the things that they are, then we can recognize that even if we don’t understand intellectually or emotionally what another person’s experience is, it doesn’t mean that it’s not valuable or that they’re not valuable as a person, or that that experience or part of their identity somehow detracts from their personhood.

MATT: Can you tell us a little bit about what you’re working on today?

LYDIA: Right now I’ve been working on developing a project called The Fund for Community Reparations for Autistic People of Color’s Interdependence, Survival and Empowerment. We call it the Autistic People of Color Fund for short.

I launched the fund last summer, 2018, using some award money that I had received from a disability rights organization, as well as the proceeds of “All the Weight of Our Dreams,” the anthology that I edited, along with two other folks — Morénike Giwa Onaiwu and E. Ashkenazy — featuring 61 writers and artists of color who are all autistic. And we used those proceeds and that award money to seed a fund that provides micro-grants to individual autistic people of color as a form of direct support and mutual aid.

The fund so far has given out over $12,000 in funds in grants of between $50 to $500 each to people from a variety of countries, as young as toddlers and as old as our elders, to help them with everything from accessing mental healthcare to covering a shortage in rent money, to escaping an abusive situation, to buying textbooks for school or art supplies or posters for a protest, and everything in between.

And that project, every several months is reinvigorated with donations from our community because we’re always running low on funds. So something that I’m working on today and this week is hoping to gain more sustainable and long-term sources of funding for the fund because right now we are in a place where the vast majority of our donations are small gifts from individual community members, many of whom are low-income or no-income, who are disproportionately unemployed or underemployed or have only precarious access to financial stability rather than having general access.

Every time I open my inbox, there’s anywhere from five to 25 emails from people who are seeking to apply for money through the fund. And we never have enough money to meet the need because our community is facing so much. And when you are negatively racialized and autistic — and most of the applicants to the fund have many other experiences of marginalization on top of that — the likelihood that you’re facing circumstances that are far beyond your control in terms of access to healthcare, access to safe, affordable and accessible housing, or simply being able to live and enjoy your life, go on vacation, see a movie is just so difficult and so hard to grasp.

And that’s something that I’m hoping we can begin to change. I know we already have with what we’ve done but it’s also not enough.

MATT: If people listening wanted to support this organization, where could they go to donate?

LYDIA: You can donate funds to the Autistic People of Color Fund by sending a check, money order, or PayPal payment to the Autistic Women and Non-Binary Network, AWN. If you donate to AWN, you’ll need to include a note that it goes to the Autistic People of Color Fund and they’ll include it in our budget.

MATT: Great, thank you. What’s your current work environment like?

LYDIA: My current work environment is in a traditional office location in downtown Washington, D.C. As an attorney, I work as a fellow for the Bazelon Center for Mental Health Law. In our offices there are 12 floors, there’s different law firms and organizations, legal and non-legal, who all share the same building. And in our office space, Bazelon is the primary leaseholder for this very large office suite.

We have seven staff currently here and we also have three other organizations, one law firm, and two nonprofit organizations that sublet space from us. So we all share this large office suite together in D.C. I’m sitting in an office right now where I have a very nice lamp that I got to replace the horrible fluorescent lights, I have a door that shuts and it’s wonderful because when I need alone time I can shut the door and when I need social time I can walk outside the door and say “Hello, my fellow workers, we all exist here, who would like coffee?”

MATT: Tell me about how traditional co-located office experiences are like for different kinds of disabled people.

LYDIA: For some disabled people, having a traditional co-located office space is a boon. It’s a boon to mental health because it enables and provides and a built-in way to connect with and share space with other humans. People were built to be in community, that is how we evolved, evolutionarily speaking, if we want to go to basic biology. And that’s true even for those of us like me who are more introverted.

People were built to be in community. And if we don’t have access to other people in our daily experiences and throughout our lifetimes we can end up living lives of enforced isolation, and that can be especially true for many disabled people, whether it’s someone who is physically disabled or whether it’s somebody who has mental disabilities or both.

Having access to a workplace where we can actually see other people, potentially have the opportunity to build social and professional networks, can be great for that reason. It can also be helpful in that if the workplace itself offers features of the building design and of the space design itself, the office layout, that maximizes access for a particular employee, it can make workflows occur better. It can make it more efficient, it can make it more easy to complete. It can enable the employee ultimately to feel better about the work that they are doing and to produce higher-quality work.

So there are a lot of potential benefits to having this type of office location. There are also, of course, downsides. And of course there are many potential configurations to these kinds of offices in the first place.

So here where I am, for the most part, we each have separate offices with separate doors. And for some folks like me that works great. Like I said, it enables me both to have privacy and to be able to work alone when I need to be alone and focus, but it also enables me to connect with others by choosing when to keep my door open and shut and choosing when to move in and out of this office space that was designated for me.

Other people who are in a co-located office location may prefer to have more of an open-office layout where there are multiple desks or workspaces that are not really separated or only have partial walls or partial dividers. It enables that same kind of ratio of having a bit of a dedicated workspace for you but also supports and enables more open conversation and collaboration with people who are physically present with you. Or to give what my partner Shain will often talk about as having a kind of ambient people existing where we’re all existing in the same space and that’s comforting in a way but it’s also not creating an obligation or a necessity to have to engage in conversation if that would be distracting or unhelpful to your workflow.

MATT: How should people think about physical disabilities versus neuro–atypical folks in regards to office environments?

LYDIA: Everyone is different, whether you are neurodivergent or physically disabled or both. And many people are both, all the time. Your needs are never going to be the same as anyone else’s, just like people who are not disabled. There are no two people who function best in the exact same type of environment.

Where disability comes into the picture is thinking about how someone’s body or mind might function best in an environment, a built environment or an emotional or communicative environment or infrastructure that perhaps wasn’t designed to begin with with that particular person’s bodily capacity or neurodivergence in mind when that design was first conceptualized and then implemented.

So when people ask me how do we then design a workplace that best fits people with physical disabilities versus best fits neurodivergent people, my response is [that] there is no one size fits all. So for example, in the autistic community, there are some autistic people who I know who need to have daily access to natural sunlight, and quite a lot of it, in order to function well. And if the room is closed off and there’s no windows or there’s very few of them, and it’s only artificial lighting, that can make it incredibly difficult to function, let alone to get work done.

And at the same time, I know many other autistic people for whom the sunlight is actually physically extremely painful and being around sunlight is emotionally draining, it is sensory overstimulating, and it physically just hurts.

Obviously those two needs are by definition incompatible. Those two people, one from each of those groups, cannot share a workspace in the same room because either one of them is very well supported and is functioning very well with that type of lighting, whichever one is there, and the other one is miserable and/or in pain. For me the question isn’t so much, “How do we design a workplace or one methodology of supporting employees in terms of infrastructure,” as it is “How do we make sure that each person that is involved with our company or our organization or our community is able to access the type of environment and space that works best for them.”

MATT: A lot of people listening here will be at or running fully–distributed companies where there is not a physical co-location place. What should people in those environments keep in mind when designing how they interact with their colleagues?

LYDIA: For the people who need to function best having more constant communication, having access to other people around them who are working or certain forms of scaffolded support from their manager, it can be hard to do that in a distributed way.

So, for example, with some people who have ADD or depression, it can be very difficult to manage one’s own workflow, which some people might say, “Well that’s a prerequisite. If you want to work for a company that has a distributed workforce, you need to be able to self-manage your time, you need to be able to self-manage your workflow prioritization, you need to be able to self-manage how you initiate tasks and follow through on tasks and insure completion. And if you can’t do that, maybe this isn’t the right workplace for you.”

And my response to that would be perhaps for some people that may be true, there may be some people who already know about themselves from their own experience that that’s not going to work for them, so those people are probably not in your workforce if that’s where you are. They might be and if they are I sincerely and genuinely hope for their sake that they are able to find an opportunity that they are excited about that will support them in excelling in an environment that they would need for them.

But for people who aren’t at that point where it’s actually an impossibility and completely inaccessible but who would struggle with the lack of formal and physical access to structure that would traditionally come with a co-located office, my suggestions would be to always go to the employee first.

If you believe that someone might be struggling with their workflow management, or they’re struggling just in general with their job, or they have already told you, “I’m really excited about this, this has been going great, however I’m beginning to have some issues and I want to make sure we intervene before those issues worsen and affect my work and affect my performance on this team,” it’s for you to ask them, “What things work well for you, what things don’t, and how can I support you in getting the things that work well?”

So, for example, if someone in a distributed company says that they need to be able to be around other people at least during part of the day to get work done, but all your employees are in different locations, then it might be worthwhile for that company to invest in paying the membership of a co-working space for that employee so that they have access to a location that has some of the features of an office — it’s a workspace, people are primarily there to do work, there might be some desks and a printer, so it can feel more like a workspace than your home or a cafe might — but it also enables that person to stay where they are and doesn’t require the company to make that investment in horrifically expensive real estate, and for a workforce that is primarily not in one location and in fact may have, at most, perhaps five employees in one location, and they don’t want to share a space together.

For somebody else it may be not so much, “I need a physical space,” but “I need to be able to have regular access to my manager, to be able to have conversations throughout the day.” In a distributed work environment, it’s not that that’s not possible, you of course already know that’s very possible, but it may be working with that employee to figure out [if] Slack work[s] for [them]. And if it’s not working for you, if it’s not meeting your need to be able to pop in and ask your manager questions throughout the day, then what are the other possible interfaces for communication modality that might meet that need instead?

MATT: It seems like this could require a big degree of self-awareness. How do people find out if they need certain environments like you describe?

LYDIA: Some people are able to figure it out better than others. And you’re definitely right that to be able to express and articulate what you need and what works well for you often requires a level of self-awareness that unfortunately not everybody has. But this is where good management and good team-building comes in.

An effective manager in a distributed work environment needs to develop the skill of asking precise and information-gathering questions to elicit this kind of information. Because even if the employee might not be able to produce this information on their own, or might know it, but not necessarily know how to communicate it in a way that would be applicable and useful in a work environment, an effective manager or an effective supervisor should be able to develop the skill of asking, “Okay, so in your last work environment, let’s talk about the setup of your office.”

Like you asked me, “Was this a good setup for you or not? What were things that you liked about it, what were things that you didn’t like about it? What was frustrating for you? What excited you when you came to work? Can you describe a time when you were really productive? What changes, if any, were made at any point during your time during this other work environment?” Or if they haven’t had a work experience, perhaps when they were in school or perhaps in some group that they volunteered with or they were part of in their community, whether it was their softball team or whether it was crochet, whatever it might be.

It’s taking some of the kinds of questions that we might ask someone either in an assessment or an evaluation and/or in a job interview, but asking them with an eye to detail, being open-ended but also narrowly defined enough to capture the kind of information that will help the supervisor, the manager, and any HR support staff in figuring out how to then apply that information into the person’s current workplace.

MATT: How common is it for people to be neurodivergent but not realize it themselves?

LYDIA: I don’t have statistics on that and part of the reason I don’t is because by definition it would be incredibly difficult to capture a number or a percentage of how many people are objectively determined to likely be some type of neurodivergent versus how many people know that about themselves.

But what I can tell you, based on anecdote and experience in working with thousands of different neurodivergent people over the last decade, is that it’s very common for people to know that they learn in a different way than others, whether that’s in a way that got them labeled stupid or in a way that got them labeled gifted.

And it’s also very common for people to have received some type of label of disability or giftedness, or both, even if that specific label might turn out to be inaccurate, but it captured some aspect of their neurodivergence that somebody observed that this person didn’t fit into the mold of what society assumes is typical of how to learn and communicate and process and deal with emotion and all of those things that make our messy stuff in our brains.

There are folks that discovered they were neurodivergent when they were in their teens, whether or not they had language for it. And there are also people who didn’t realize it until their forties, fifties, sixties, and even seventies. I’ve met some people in their seventies and eighties who figured it out at that late stage in their life.

And it tells you a lot about us as a society of how we simultaneously assume that you don’t really count as disabled or neurodivergent if it’s not affecting you in a way that we treat you horribly over. “Well you must have functioned fine.” They probably didn’t, they were just very good at trying to hide it when they weren’t. Or that we say we knew about it so we labeled you all kinds of derogatory and terrible things, we recommended you for institutionalization, we assumed that you would never be able to make your own decisions, never be able to choose and form your own relationships, anything like that.

And either way, neurodivergent and other disabled people will find ourselves in the double bind of being expected to overcome and mask being disabled for the comfort and convenience of non-disabled people or of being assumed that we will never amount to anything by any definition, that we are completely incompetent, that we are incapable, that we don’t belong and that we shouldn’t belong. And it’s always one or the other.

But really they boil down to the same kind of ableism and that ableism is the devaluing of disabled people’s experience, that to live life as a disabled person of any kind means that we’re living a lesser life. But the reality is, is that disabled people have so much to offer ourselves, our own communities and the entire rest of the world because we have lived our entire lives learning how to function and survive and sometimes, when we’re lucky, to thrive in a world that was literally designed not for us.

MATT: I have heard of workplaces that actually target and try to hire disabled people. What are some of the superpowers that those companies might be trying to benefit from that people might not appreciate?

LYDIA: You know, it’s really interesting every time we talk about disability-targeted hiring initiatives for me because there’s a lot of cognitive dissonance. On the one hand, many of us appreciate that there are companies out there that are trying to seek out more of us to hire us, recognizing that we actually do have talents and capacities individually and perhaps to some extent there may be some patterns of some talents among some people, at least sometimes. And that’s great, especially given the astronomical rates of un- and underemployment for disabled people, especially those of psychosocial, intellectual, and developmental disabilities.

But at the same time something that really worries me in many conversations around employment and corporate hiring initiatives are that many hiring managers creating these programs will say things like “We love having disabled employees because they’re so motivated, they show up to work every single day, they never call out sick, we can depend on them, they’ll be loyal to our company forever.”

And you know, at the surface level, when you don’t really think about that too deeply that sounds great. Like, yeah, that means that disabled employees tend to be really dedicated, we should hire more disabled people. But what that says to me is actually that because of our astronomical rates of un- and underemployment, we have become sometimes an exploited labor force.

Where there are some companies that mean well, they’re not necessarily doing this out of malice, but they are aware at least on some subconscious level that it’s more risky for many disabled employees to call out more. That it’s more risky for us to do anything but excel far above and beyond what our non-disabled peers need to do in order to make sure that [we] keep [our] jobs.

And that makes me really sad and it makes me really angry. Because I don’t think we should be hiring disabled either because of stereotypes that might or might not be true, e.g., that all autistic people are savants at math or that all blind people are prodigies at music, when sure, some are. There are some autistic people I know who are math geniuses and there are some blind people I know who are incredible musicians and there’s also plenty of us that aren’t. Like, I’m autistic and I suck at math. Also I’m Asian so I just broke two stereotypes at once, which is fun. [laughter]

We all have different skill sets and they may or may not be tied at all to our disability but we should be hiring people based on whether that person is going to be able to do the job and do it well, disabled or not. And we should be hiring people because we want them and we believe that they belong in our workplace, we want to support them in being part of that workplace, and as being more than a person who simply does a job but as someone who belongs to the community of people in this workplace. That’s what we want to do.

And so if the question is, “What are superpowers that we bring?” My answer is, how about we not talk about superpowers but we talk about why each and every single one of us deserves to be able to do work in a way that’s meaningful, that makes sense, that makes us feel good, that is not doing something horribly unethical, hopefully, and that at the end of the day enables us to be able to live in a system that unfortunately isn’t really set up for most of us to thrive?

MATT: Let’s talk about why — why people deserve to have that.

LYDIA: I believe very firmly that every single person deserves to be able to live in a safe community and to be able to live a self-determined life and to be able to live authentically and true to themselves and to be able to live as part of a community where they can receive care, they can receive support, they can receive love, and they can feel a sense of belonging.

And I believe that that is inherent to human dignity. It should never have to be earned. Somebody should not have to earn the right to live without fear of violence. Someone shouldn’t have to earn the right to be able to afford safe and accessible housing. Nobody should have to earn the right to be able to receive healthcare.

And unfortunately in the society that we live in our society presumes that those are things that need to be earned and that if we don’t think someone is contributing enough or we don’t think that they are productive enough, that maybe they don’t really deserve those things. And if we’re nice, maybe we’ll give it to them, at least a little bit or at least for part of the time, but until and if and when society says, “Oh, you’re pulling your own weight, we think it’s contingent and we think it’s conditional.” And that to me is incredibly inhumane and unjust.

MATT: As a wrap–up, was there anything we missed that you wanted to talk about? 

LYDIA: I just think it’s important to note that when we’re talking about employment and disability, I believe that the corporate sector has an opportunity to take leadership in fighting for fair and living pay for people with disabilities. Many people don’t know that it is still 100% legal in the United States and in many other countries around the world to pay people with disabilities pennies on the hour or the equivalent.

MATT: Really?

LYDIA: In the U.S. it’s emblazoned into federal law, in section 14(c) of the 1938 Fair Labor & Standards Act. Section 14(c) is still on the books today and there are many for-profit and not-for-profit organizations that take advantage of section 14(c) to pay disabled people as low as cents per hour for menial labor and it’s 100 percent legal. And this is horrific.

There is a bill before the Congress right now called the Raise the Wage Act, which, if passed, would eliminate the use of what’s called sub-minimum wage in the U.S. And that’s pretty awful that such a concept exists. If it’s minimum, there is supposed to be nothing below it. But in the U.S. we call it sub-minimum wage.

There are other nations in which there are no labor protections at all for people with disabilities, either in terms of non-discrimination or wage protections. And while I’m not an expert on international labor law, what I do know is that companies around the world, all of the folks that are listening here, have an opportunity not only to prioritize and speak publicly on ensuring that you’re paying folks a living wage and a fair wage that is not based upon backward notions of productivity, but also to fight for the end of sub-minimum wage and other unfair labor practices that devalue disabled people’s work even more.

MATT: If people want to follow you more, where can they find you online?

LYDIA: You can find me on Facebook under the name Lydia X. Z. Brown — Autistic Hoya. And you can also find me on Twitter @autistichoya. All one word. My home page is autistichoya.net. And my blog is autistichoya.com. That should really be reversed but that would require a type of web engineering that I am not capable of doing alone. [laughter]

MATT: Well I’m also very honored that you use WordPress for many if not all of your websites.

LYDIA: I use WordPress for almost all of my websites and I love it.

MATT: Awesome, I very much appreciate that. Finally I will mention as well what you said earlier. Autismandrace.com, which is where they can donate to the project and fund that you mentioned earlier. And there are some instructions on that website for how to do so.

MATT: That was Lydia X. Z. Brown. You can find them on Twitter at @autistichoya. That’s @ “Autistic” and then “Hoya,” H-O-Y-A. You can also find Lydia blogging at AutisticHoya.com. 

It’s really important for folks who run distributed teams to remember that employees don’t fall into binaries of “normal” or “abnormal.” We all find ourselves in different spots on different spectrums of ability throughout our careers, and hopefully, with more flexibility around workspaces, work hours, or work styles, we can all feel included and productive no matter what professional setting we’re in. 

On the next episode of the Distributed podcast, I’ll be speaking with Clark Valberg, the CEO of InVision, which is a very popular cloud-based design platform that many distributed teams, including Automattic, have adopted. InVision started out as an agency, but after they built this internal tool for their designers, they realized that it was big enough to be a flagship product. InVision is similar in size to Automattic, so I’m interested to hear about Clark’s distributed journey. 

Thanks for joining, and see you next time.

Read more about Taso Du Val in “Inside Toptal’s Distributed Screening Process.”

When hiring managers interview a candidate for a high-level role, they want to be sure that the person they choose will be productive and able to work well with their prospective team. But what if the hiring process takes place over video chat? A growing number of companies outsource the vetting process to a company like Toptal, a freelance marketplace. Toptal’s CEO Taso Du Val joins us on this episode of the Distributed podcast, with Matt Mullenweg. 

The full episode transcript is below.

***

MATT MULLENWEG: Howdy. My name is Matt Mullenweg, and I run a company called Automattic, with over 950 employees distributed across over 70 countries. We’re growing quickly, so I spend a lot of time thinking about how the company is going to find the very best people. Since our team leads might never meet a far-flung applicant face to face until well after they’ve been hired, our hiring process has to be comprehensive, so sometimes it can be a little bit of a slow and long process.

But what if you need to hire top talent quickly? What if you need a world-class project manager on a short-term basis, and you don’t have time to rigorously vet a bunch of applicants or set them up on a payroll platform? 

Well, you might turn to Toptal, a freelance marketplace that aims to provide companies with a fully-vetted pool of talent that represents the top 3 percent of their network’s applicants. Toptal’s CEO, Taso Du Val, joins me today to talk about how he built his company, which happens to be distributed all over the world, and about how current approaches to recruitment are undergoing a major sea change.

Let’s get started. 

MATT: All right, we are here today on the latest episode of Distributed with Matt Mullenweg, and we have CEO and Founder of Toptal, Taso Du Val. Welcome very much.

TASO DU VAL: Thank you, Matt, for having me.

MATT: Just for listeners who might not know what Toptal — do you mind explaining your journey to Toptal and then you can introduce what Toptal is?

TASO: I was doing some consulting work and working with some companies doing contract software development, and at the time I was mentioning to them that they should use some other resources to be able to get software developers. I mentioned the freelance marketplaces on the internet. And so many times they said to me, “Those are terrible places. You can never find good resources there.” 

Meanwhile, I was having a great experience finding great resources there. So I said “Hmm, this is fascinating, I keep hearing time and time again that people are having terrible experiences finding top talent, yet I’m having a very consistent experience finding top talent. What is the difference?” And the difference really came down to my domain expertise, being able to identify and screen that top talent. And that was really the genesis for what Toptal is today.

MATT: And your background, like myself, is engineering.

TASO: Precisely.

MATT: And in fact, we met at — was it a MySQL open source conference 14 years ago, or something?

TASO: Yes, in 2007, 2008, after the first MySQL camp at Google. So that was a really long time ago. 

MATT: So Toptal is, if you were to summarize it, a site I can go and say, “Hey, I want X, Y, Z?”

TASO: Mhm.

MATT: You cover a few areas now — developers, designers…?

TASO: Project managers, product managers, and finance experts. We just launched recently project managers and product managers, and that has been phenomenally successful. So I would say the demand and the experience that people are having with product and project managers far surpassed what we thought it would by a long shot. So it’s been really cool to see a management type of role take place remotely and be so successful. 

With developers, they have a long history of working remotely, even designers, and that is in part because individual contributors can contribute more rigorously to a project. You have, in the case of software development where you can commit code, in the design world now lots of tools are evolving to be something similar.

MATT: InVision, Figma, and things like that.

TASO: Precisely. So if you look at it from that perspective, it’s very conducive to the remote working process. When it comes to management, it’s still a little bit new, of course not for us internally, and for many distributed companies, but for outside consumers it’s a little bit more new. They’ve been very receptive to it, and it has worked really, really well, more so than we anticipated.

MATT: So if I’ve got a job to be done, I can go to Toptal. I hire someone, and I can now hire someone to come into an office, or is it all through the platform?

TASO: We do some on-site work. Generally what we do is 95% remote. And so when a client or someone wants someone on site for a certain period of time, we allow for that, however we are not generally the conduit for facilitating on-site work.

MATT: The advantage of going through you all versus just finding freelancers, is you ensure the quality of the talent?

TASO: Mhm.

MATT: And you have tools to mediate the experience, right? I don’t need to worry about how they’re getting paid, I could just pay you and you take care of it all?

TASO: Precisely. And I would say the biggest value-add is the time it takes to acquire the talent and the energy it takes to screen the talent. We have done all of that for you. And so — no kidding, this is a real stat — our send-to-hire ratio is about 1:1.5. For every 1.5 “candidates” that we send you, you will hire one of them.

MATT: Oh wow.

TASO: We aren’t a recruiting shop, we aren’t a typical staffing company whereby we send you ten resumes and you say “Okay, I want to screen and talk to all these folks.” We generally send you one. And the reason that we are able to do that is because we actually have a lot of process and domain expertise internally to be able to vet those talents, whether it’s in finance or software development, to ensure that that person, before we send them to you, is the perfect match.

So it’s about getting information from you up front in a more modern way than a staffing or recruitment company generally does it, and then facilitating the matching process through software and processes that are reinforced through software. 

MATT: Let’s do some level setting around the company. I know you’re private.

TASO: Yes.

MATT: But to whatever extent you can talk publicly about how many people is it, how many people are on the platform? If you can talk about revenue at all…? Just to give the listeners an idea.

TASO: In terms of a core team we are approximately 500 full time internal folks. Those folks work on software development for our platform, for the website, for different technologies that help facilitate the screening and matching processes, and so on and so forth. And then we have other folks who work in operations, marketing, and so forth. So that team is about 500, let’s say.

MATT: Were you distributed from the start?

TASO: Yes, we were distributed from the start. I started the company on a handshake and then contracting out a software developer to a company almost without a website. So that is really how the company started. And I was in Palo Alto at the time. The individual who was contracted out — actually, we pretty much had two — were in Argentina and South Africa. And I was actually going to an office that my roommate’s family’s friend allowed me to have as a way to go to work everyday. 

However, the point was rather moot. I was going into an office but not seeing anyone or interacting with anyone except myself. So it almost was this zombie-like walk to the office every morning where I’m going to the office because I go to work, but I don’t see anyone who I work with. [laughs] And so I actually started waking up and just working on my computer at home. 

And then I said to myself, “Well why am I even working from home? I should just go somewhere else because I’ve never really traveled!” So I ended up going to Europe and all sorts of different places. And that’s what took me on my remote journey, so to speak.

MATT: So, FotoLog and Slide, places you were before, did those have distributed teams or were they mostly co-located?

TASO: Those were in-office companies. I went into the office pretty much everyday. The remote working nature was there, but it was very light.

MATT: So 500 people. I know a couple years ago you said it was over $100 million revenue, so I imagine it’s beyond that.

TASO: Yes, and this year we are likely to be in the nine figures in net revenue, which is a really big accomplishment for the company.

MATT: Congratulations, that’s huge.

TASO: Thank you, yes.

MATT: Again I think it’s good to set this up because not that many people know about Toptal yet. 

TASO: [laughs] Well said.

MATT: And after this podcast, at least dozens more will.

TASO: A few dozen, a few dozen.

MATT: One of the worries people have about building distributed companies and distributed work is this hiring aspect. How does that work for you all? How do people find you? How do you screen them? What can you tell us about that process?

TASO: A lot of people find us through our brand. Freelancers find us in different countries as we are generally the best source for them to get good jobs remotely, especially within the United States and with Fortune 500-type companies, companies that are doing more serious engineering work and are longer-term engagements. 

So our reputation has permeated in those types of environments on the talent side. On the client side, I would say it’s similar. Now, of course we do marketing, however, we do often have referrals, and word of mouth is a strong way that we get a fair amount of business. So those are, on both sides, really how people know about us, generally speaking.

MATT: How many applications do you all get?

TASO: Oh my gosh. Here’s an interesting stat actually. At this point in time, I believe, and I’d have to double-check this, it’s over a million a year.

MATT: Wow.

TASO: And to put that in perspective, Google as a company gets approximately 1.2 million applications a year as a company. 

MATT: Wow.

TASO: So if you look at it from that perspective it’s actually a pretty sizeable volume. It is a little bit apples and oranges because all we do is screen talent, that’s it. 

MATT: But it probably speaks to how much global talent there is looking for remote opportunities, which is one of the big advantages of being in a distributed company.

TASO: It does. And that is kind of the miracle of it, I suppose. While we are doing a million applications a year, I think that absolutely pales in comparison to what’s out there and what we could do if we put even more effort behind it. My assertion, if we went pedal to the metal and we started doing a lot more advertising, we actually worked to amplify it, I think we could get easily four to five million applications a year globally. If you think about —  

MATT: Wow. I can’t imagine that applicant tracking system.

TASO: [laughs] Well we built our own because all the other ones were certainly not sufficient. If you think about it from that perspective, that not only highlights the amount of people that are talented all over the world but it also highlights the amount of people that want to work remotely that are not today. And so the far majority of our applications want to work remotely, meaning they are not working remotely today but they are applying because they see it as a huge, life changing opportunity for them. And so it’s really interesting to see the dichotomy between what is today versus what we’re seeing people want tomorrow to look like. 

MATT: So I’m an engineer somewhere, I want more flexibility, I go on Toptal. Let’s say my resume makes it through. How do you determine whether I’m top two, three percent or not?

TASO: Well it’s a subjective process, and so I can’t state it’s perfect, but we err on the side of conservatism so that we have a near-guaranteed great experience for our clients, in a similar sense that McKinsey does or that some other top-tier firms that offer top talent, so to speak. The real high-level deals are that you go through what is in effect an interview process.

MATT: Like you’re going to be hired?

TASO: Like you’re going to be hired at a Google or a McKinsey or a company like this, depending on the vertical.

MATT: How important are their technical skills versus their people or soft skills?

TASO: They are both incredibly important to us. So we have looked at, for example, how McKinsey screens people. And we have actually taken some of those processe and refined them and introduced them into our screening processes. Same with Google, same with some other companies that are keen on hiring good cultural fits. I wouldn’t say in terms of our own network there is a unified culture, but there are certainly elements that unify people in terms of soft skills. 

They have high integrity, they have punctuality. No kidding — something we screen rigorously for. They have good judgment, which we are able to screen for in different areas. So if you think about elements like that, you can actually screen well beyond hard skills. Do you know how to write an algorithm in constant time versus quadratic time, or something of the nature like this, which is still a very important skill to have. But I would actually say the soft skills are, especially when working remotely, more important.

MATT: So even if I’m a brilliant engineer, if I show up late to your interview, it’s going to be a mark against me and you might not hire me if I don’t have those good soft skills?

TASO: Oh 100%. The punctuality component is very, very real. So if you show up just a little late you will literally be rejected automatically. 

MATT: Wow.

TASO: And people get pissed on this point. They’re like “Hey, I was on another call, I went through the—” Hey, look, that’s our integrity on the line. If McKinsey and the best companies have survived by upping the bar in terms of integrity, we’re going to do the same.

MATT: I was going to ask how you test for integrity, and punctuality is an interesting window into that.

TASO: Yes.

MATT: What are some other things that you feel like are really important to the Toptal culture?

TASO: One element that I can speak to is the character of the person. As many people know, great engineers can be very abrasive. And I would say there was a point in my life, if not still in many cases, I can be abrasive. But if you go into an interview process and you understand it’s professional, you have to show your best self. And if you are abrasive when you’re showing your best self, it doesn’t go uphill from there. Right? [laughs] It kind of goes downhill. 

So you have to be very judgmental on those factors because if they are introduced to a client that then experiences Toptal as a group of abrasive but brilliant people, that’s not going to resonate with them very well. So you have to take elements like that, that are a little bit more subjective, a little bit more nuanced, and factor them into the equation, because it’s not just about whether you can write algorithms or not.

MATT: Like all distributed workforces, like your own, for a lot of people English is not their first language.

TASO: Correct.

MATT: So are there resources you point to or anything or is that something people need to learn on their own?

TASO: Internally at Toptal, we have provided English lessons before. We don’t anymore. But it’s generally something, both in our core and externally in our network, that we expect people to know coming into Toptal, whether that’s through our network or through the core team.

MATT: I actually was pitching this to Austin from Lambda School. Part of what they’re doing is taking people who don’t know how to code and teaching them to code.

TASO: Sure.

MATT: I think there’s a huge opportunity in that there are probably millions of great engineers who are great coders and don’t know English well.

TASO: I would say that’s the case.

MATT: So versus teaching someone how to code, teach them English. I don’t know which is harder, to be honest. They’re both learning a language, just an artificial versus natural language.

TASO: We have thought of putting people through different re-skilling programs. However, I’ve never thought about it as well — if you already know blockchain but you speak Chinese, can we just teach you English and will you be able to work with people internationally?

MATT: How do you decide if who you’re hiring goes to the Toptal internal team versus clients?

TASO: It’s very separated. It’s very separated so that we have clear client expectations and KPIs and we have clear internal KPIs in processes. You would think we would mix them, that we would leverage the incredible technology that we’ve built for our network, but it wasn’t so easy to compartmentalize. 

MATT: So Toptal itself is not a client on Toptal?

TASO: We are in some instances but we are not using it to the extent that people would think we would use it. 

MATT: When you say KPIs, what are the differences?

TASO: We are looking at time to hire, time to fill, so on and so forth. So we would have to disable all these components. In regards to how we do our screening we have capacity, metrics and triggers that exist in there to help manage the pipelines. It’s a really big system, rightfully so, for Toptal the network. Internally it’s a little bit difficult to decouple from the purpose that it has already been constructed to serve.

MATT: Let’s zoom into the virtual wall.

TASO: Sure, sure.

MATT: Tell me a bit about how the company is set up. Who are your direct reports, how is your hierarchy and what’s your structure? How should people think about Toptal?

TASO: Let’s kick it off with how the company operates. I think that’s a good window into how we work and gives you some good insights into how structured we are, how we set goals, how we actually work day-to-day. We have an OKR method that we use, like many companies, to set objectives quarterly, annually, so on and so forth, and we are very rigorous about it. We are very methodical about it.

MATT: As CEO you have some OKRs and those..?

TASO: I do, yeah.

MATT: What are some off-the-shelf tools you use?

TASO: Slack, Zoom. In terms of product management we use Jira. What I find really interesting is Confluence. I find Confluence very interesting.

MATT: That’s their internal blogging thing, right?

TASO: It’s actually more like a Wikipedia slash — 

MATT: Yes, like document management plus some internal —  what I would call blogging, but you can use it instead of email, right?

TASO: Right. It’s still a little bit cumbersome, still a little bit big in some instances, but it is a really good tool.

MATT: I know Atlassian runs on it religiously.

TASO: Yes.

MATT: They say it’s their secret weapon, it’s the thing that makes everything work.

TASO: We’ve started to go down that path actually for knowledge management, and for documenting processes, and for other elements that are important for the company to be unified on. 

MATT: So those are some off the shelf ones. Any others that come to mind? Google Apps, Office 365?

TASO: Yes, Google Apps. Yes, I would highly recommend it. [laughs]

MATT: Yes, it’s pretty good. They did a good job there. Who’s on your exec team? How did you meet?

TASO: Sure. So our executive team is pretty traditional. It depends if you’re looking at a more traditional company or an internet company. We have a fair amount more executives that report directly to me. That’s a personal choice.

MATT: So is it flat at the top?

TASO: I have about 12 direct reports. And from what I’ve seen via conversations and from what other companies are doing, that tends to be on the larger side of things. I have seen companies with 20 and I think we even had 20 at one point, not realizing how bloated that was. And so we — 

MATT: So what reports directly into you? Is there a CTO, HR?

TASO: CTO, CAO, we have a chief administrative officer, that person is really working to refine all the processes, the data analytics, business insights. A VP of people, a VP of brand marketing, a VP of growth marketing, a VP of design, a VP of comms, a VP of finance and probably two others that I’m missing.

MATT: How do you all get together? Where are those people located?

TASO: Well our VP of finance is in Pennsylvania. Our general counsel is in Massachusetts. Our VP of product is in Greece.

MATT: So these people are all over the world.

TASO: They are all over the world.

MATT:  And do you meet weekly, every other week?

TASO: We meet biweekly, so every two weeks we have meetings. And that is the cadence at which we meet. We also have an all-hands that’s monthly. And so that gives you insight into how often our all-hands occur with our company.

MATT: We do a similar thing where once a month we do — we call it a Town Hall. Typically the questions come in via text but everyone is on video now. We can all be on Zoom. You can get hundreds of people on Zoom pretty easy now and it’s — so sometimes they come in real time. I really like it. I also enjoy not knowing what’s coming next. We don’t pre-moderate or pre-screen the questions or anything. It’s just whatever pops up at the time. Everyone sees the question being asked. It’s not like I can skip them if I don’t like it. And sometimes the conversations are difficult, sometimes the answer is “I don’t know” or “Maybe we made a mistake,” or things like that.

TASO: Right. We used to do it via text. Now we’ve just chosen to do it in a free-form style, so that it’s a little bit more engaging. We also had a method by which you could do it anonymously, which we have totally abolished across all of Toptal. We don’t have anyone have anonymity. And while I understand that there may be ramifications of people not being as forthcoming as they may, it’s really our duty to ensure that we create an environment where they can be. 

MATT: When did you do that and why?

TASO: We did that because you’re actually taking an action that encourages hiding and we don’t believe in hiding anything. We believe in radical transparency, radical truth, bringing difficult conversations and difficult topics to the forefront. And by taking that action, you’re saying “We actually believe in hiding something.” Well I don’t believe in that and I would say our executive team doesn’t believe in that, so we have abolished it.

MATT: When did you abolish it?

TASO: About seven or eight months ago.

MATT: Pretty recent.

TASO: Yes.

MATT: I’ve got some quick ones as we wrap up. Tell me quickly what is your ideal workspace? Where are you productive?

TASO: I am productive sitting at a desk I am familiar with. 

MATT: Do you have a big monitor? What’s your — 

TASO: I don’t have a very big monitor, I have a regular sized monitor, but I’m just familiar with the setting, it’s something about the familiar setting that allows me to be focused. So if I’m in a hotel room, my first impulse I suppose, is to get out of the hotel room, go to a meeting, go connect with someone because you’re traveling. It’s not to sit down and focus and go through Excel and dive deep into the nitty-gritty details of whatever it might be, whether they’re financial reports or they are reports about whatever it might be, and scrutinize them.

Likewise, when I’m on a plane, I’m always reading. It’s just my natural state, so to speak, on a plane. And so whenever I’m at a desk that I’m familiar with, with my computer that I’m familiar with, I can do work much more productively.

MATT: How often would you say you’re home versus on the road or traveling?

TASO: I’d say it’s 80/20 now. So I am more so settled, working, than I am traveling.

MATT: That’s a good thing to note, that a lot of people think remote or distributed means you’re on the road all the time.

TASO: Oh no.

MATT: And actually I think the vast majority of people at Automattic at least, they’re in the same place 95% of the time.

TASO: 100%. 

MATT: How about meetups? When does your team meet up in person, if ever?

TASO: Yes, our executive team probably meets up on average every 18 months. So not so much, but I don’t see it as a requirement. When we meet up, it’s generally when there are some executive changes and we are unfamiliar with one another. And so — 

MATT: And are there other meetups within the company?

TASO: Yes. Actually, as we’re speaking right now there’s a function that’s having a meetup in Miami.

MATT: So like all the designers, all the engineers might get together, something like that?

TASO: Precisely. It’s a little bit too large for the engineering team, being about 200 people, to be able to do that, but yeah. On a functional basis, especially with some of the smaller functions, they’ll be doing that.

MATT: Do you have any must-have equipment that makes for ideal work?

TASO: A laptop and a phone. [laughs]

MATT: That’s it? Nice. You mentioned Zoom, Slack, phone? Do you make phone calls? Do you talk to people? How much are you on text versus video, versus audio?

TASO: I would say I have moved to mostly video. When I’m mobile I don’t do video generally because my battery is dying. [laughs] But generally I’m on audio when I am traveling and I’m on video when I’m situated.

MATT: Last question. Let’s fast-forward 20 years from now, what percentage of jobs do you think will be distributed or remote?

TASO: I believe that at least 50% of all technology jobs will be distributed.

MATT: That’s wild. Because it’s probably, I don’t know, what is it today? Probably under 10%?

TASO: It’s under 10%, but it is growing so fast and there is such a strong movement across the world for this. You have all of these strange companies, Toptal, Automattic, InVision, GitLab, so on and so forth.

MATT: We’re not that strange. [laughter] But I get what you say. Right now it’s the exception. In the future I think it’s the rule.

TASO: Exactly. And they’re looking at us saying “Okay, yeah, they created a billion dollar company. It’s a billion dollar company, we’re a $200 billion company. This is hogwash,” right?

MATT: It’s a toy. Yeah.

TASO: Well more and more people are doing it. More and more people are picking up on the fact that this is the future and that is becoming more and more compelling to the talent. So more talent are keen on working for those companies — the Toptals and the Automattics of the world. And that’s just going to grow. 

So what’s going to happen is, all these small companies where they’re working remotely, well actually that’s going to be the majority of the talent in the world. And when these companies can’t recruit them anymore and there are millions of people working remotely that are skilled, and they’re saying, “Well we want you to work in our office,” they’re going to say, “You know what? I don’t work for companies like yours because you’re the old, stodgy company. You’re the company that doesn’t understand the future and opportunity and innovation.” And that’s when it’s going to come and force them to be remote.

So you’re going to see that happen because the workforce of talented people is going to be more keen on remote work than not. And people don’t see that now but once they’re unable to recruit at all from anywhere, in effect, that’s when the change is actually going to happen.

MATT: Amen. [laughter] I think that’s a great place to end it. Thank you again, Taso, and I hope to continue this conversation in the future. 

TASO: Thank you.

MATT: That was Taso Du Val, and I’m very glad he was able to join and share his experiences. 

On the next episode of the Distributed podcast, I’ll be speaking to Lydia X.Z. Brown. Lydia is a lot of things: a writer, advocate, organizer, strategist, educator, speaker, and attorney. I’m interested in talking with Lydia about how distributed work can make work more accessible to people with all kinds of disabilities, and learning more about what inclusion means in a distributed context. 

Thank you so much for joining us, and see you next time. 

Read more about Stephen Wolfram in “The Machine that Turns Ideas into Real Things.”

Stephen Wolfram started out on an academic career path, but eventually realized that founding a company would allow him to pursue his scientific work more efficiently. He’s served as a remote CEO of Wolfram Research for the last 28 years. In this episode, Stephen shares with host Matt Mullenweg — another remote CEO — his perspective on the value of geo-distribution, and the processes his partially-distributed company uses to make world-changing software. 

The full episode transcript is below.

***

MATT MULLENWEG: Howdy, howdy. Welcome to the Distributed podcast. I’m your host, Matt Mullenweg. 

I got the chance to catch up with today’s guest, Stephen Wolfram, because my company Automattic invited him to give a talk at our annual company meetup in Orlando, Florida. This is a magical occasion where all 950+ Automatticians (which is what we call ourselves) get together to meet up face-to-face. This gives us an opportunity to hang out, break bread, and collaborate over the course of a few days. We also invite a number of speakers, smart people like Stephen.

Stephen’s been leading Wolfram Research for 32 years, which is a really long time for a tech CEO. The company has pioneered a lot of different technologies in computation and education. Wolfram Research has about 850 employees, many of whom are scattered across 29 countries, so it’s pretty close in size to Automattic. 

But Stephen’s been doing the remote CEO thing for way longer than I have — about 28 years! So naturally I wanted to pick his brain, which is an amazing brain, on why he chose to go the partially-distributed route, and learn about how he’s led his company remotely for longer than just about anybody. 

Alright. Let’s get started. 

MATT: Welcome. This is Distributed with Matt Mullenweg, and today we have Stephen Wolfram, who is the Founder and CEO of Wolfram Research, known for things such as Mathematica, an amazing tome called A New Kind of Science — which I guess you worked on for about ten and a half years — created Wolfram Alpha, which is one of the intelligence engines behind Alexa and Siri…

STEPHEN WOLFRAM: Siri and other things, yeah.

MATT: Yes, and of many other things. And just an incredible amount. I encourage you to google him. Go down the rabbit hole of all the amazing stuff and people he’s worked with and everything. Thank you so much for joining today.

STEPHEN: Nice to be here.

MATT: Part of the reason, in addition to all those fun things, that I wanted you to be here is your company is a similar size to Automattic, around 800-900, and is geo-distributed as well.

STEPHEN: Yes.

MATT: You have been a remote CEO since 1991.

STEPHEN: That is correct.

MATT: And your company goes back to..?

STEPHEN: Late ’86.

MATT: Possibly one of the older geo-distributed companies I’m familiar with.

STEPHEN: I think so. I mean, I know —  

MATT: It’s got to be one of the longest, if it’s not—  

STEPHEN: Yes, you’re right.

MATT: Maybe there’s something out there but that’s got to be one of the longest.

STEPHEN: Right.

MATT: That’s pretty cool. What caused you to be geo-distributed at the beginning?

STEPHEN: So OK, the first thing was, I started the company. This was the second company I started. The first company I started, I started when I was 21 years old and that was in Los Angeles, and that company was a pretty traditional company. It was venture-capital funded, I brought in a CEO, I didn’t CEO it myself, I was the technical person —  

MATT: Did they call it adult supervision back then?

STEPHEN: No, no they didn’t. I mean that company went through various mergers and things and eventually went public some time in the 1990s in a very undistinguished IPO. So anyway, so my first company was not distributed at all, it sat in this building near the Los Angeles International Airport. [laughter] 

I was involved in basic science and I had developed this area of science that I guess now gets called complexity theory, and so I tried to figure out what university would give me the best deal to start a research center in this kind of science. So I went around to lots of universities, and the one that won that was the University of Illinois in Champaign, Illinois. But I said, “OK, I’m going to start a company that builds the tools that I want to have for myself and that I perfectly well know are going to be useful to lots of other people in the world.”

So we started the company in Champaign, Illinois, which is not probably most people’s first choice for where to start a tech company, even back in 1986, but it was great. We got terrific people from the area — it’s a good university, producing a lot of interesting graduates. We were the only game in town, so to speak, and I think we’re still the largest tech operation there. So we started in a slightly outlying place. Then [we] got off to a very quick start, up to a couple hundred employees, maybe 150 or something. I was injecting ideas into this thing at a very high rate.

MATT: So when you inject ideas, you’re coming and saying, “Hey we should do this thing.”

STEPHEN: Yes. And getting more and more frustrated that they weren’t getting done. I have to say that just a few years ago we finally finished my 1991 to-do list. 

MATT: Ha! [laughter]

STEPHEN: So it’s done, that one is — it finally, finally happened.

MATT: That one’s… Yeah, the thing that got you to leave is now all the way complete. 

STEPHEN: Yes, right. My original plan had been to build these tools that will, among other things, allow me to do the basic science that I wanted to do. I said, “Let me step back a bit and let me go off and spend some chunk of my time doing basic science, and let the company grow up and we’ll see what happens next. Maybe there will be a coup and somebody else will say ‘I can run this better than you can’.”

MATT: So everyone was in the office except for you?

STEPHEN: Not quite. What happened was — I’m trying to remember how many people weren’t in the office at that point, but I was definitely the main go-offsite person.

MATT: What were the tools at that time? Was that because you had been in a university setting and were familiar with email or internet?

STEPHEN: Yes, well I started using email in 1976. So that was —  

MATT: That was pretty familiar to you.

STEPHEN: Yes, right. It was modems dialing up. My email would arrive in bunches every 15 minutes. And I was on the phone a bunch. I had hired a chief operating officer.

MATT: I was going to ask what the exec team looked like. You had a COO who could be the on-the-ground lead?

STEPHEN: Right, who was with us for six or seven years. And he did a good job of maturing the company from being high-growth to something which had good systems in place and could roll forward. 

MATT: And this second iteration of the company, did you also raise venture capital, or did you decide to take a different approach to have the longevity?

STEPHEN: No, no, not at all. Version two — I was the CEO from the beginning and forever type [of] thing, no outside money ever. It’s been a shame for me that I’ve never really had a quote “business partner.” I think of myself as pretty average at business kinds of things but I’m not totally incompetent. 

Personally I view it as an optimization. You can do things that are very commercial, but a little bit intellectually boring. And it tends to be the case that you’re doing a lot of rinse-and-repeat stuff if you want to grow purely commercially, so to speak, or you can do things that are wonderful intellectually, but the world doesn’t happen to value them and you can’t make commercial sense that way. And I’ve tried to navigate something in between those two where I’m really intellectually interested and where it’s commercially successful enough to sustain the process for a long time. 

MATT: I love finding that intersection.

STEPHEN: Oh yeah.

MATT: And it feels like now that the world has caught up a little bit to voice assistance and the natural language processing stuff you’ve been working on forever, that you found — is that the main business model for Wolfram Research now?

STEPHEN: No, no.

MATT: Oh, I would’ve thought that licensing drove it because there must be billions of users of these voice assistants.

STEPHEN: There are. Yes. And it’s a good source of revenue. At this point it’s fairly diverse. There’s a big chunk of licensing software but a lot of that — there’s, for example, the academic sector, there’s site licenses to universities where basically the goal is to make the software free for people to use at universities, and we’re complete now in the U.S. in the sense that all the major universities have site licenses. So if you’re any kind of major university in the U.S., you will be able to use our software for free. And there’s a lot of commercial use of software where we’re basically selling pre-packaged software. It’s been nice that it has been gradually quite diversified between different kinds of channels. 

Back to the whole no venture capital do. It’s been great. I don’t have a boss. I recommend it. [laughter] And also I can do things —  

MATT: I feel like you always have a boss. It might be a customer or all of the customers in the world. 

STEPHEN: Yeah, at some level —  

MATT: It could be the employees for whom you’ll respond to if they reach out.

STEPHEN: That is correct. Yes, that is really what happens. But in the first approximation you think, “Oh, I can do anything,” and then the second approximation is, “Oh, we have all these customers. Oh, we have all these employees.” I take those responsibilities really seriously. But I’ve been doing them so long that they seem natural, so to speak. It’s a thing where there is a certain kind of intellectual freedom, that I at least believe that I have by virtue of the fact that I’m just responsible to myself.

MATT: I will say that I think, as a result of so much capital flooding into the market, that there now are very long-term investors who, if you choose them correctly, can be aligned on longer time spans than the standard five to seven [year] fund life of some of the historical venture capital.

STEPHEN: Right.

MATT: And founders now are able to retain a lot of control through voting mechanisms. They might sell economic interest but [you’re] no longer selling control interest.

STEPHEN: I always wonder how that’s going to come out in the end. I thought about taking my company public back in the early 1990s. We were on a great trajectory and etcetera, etcetera, etcetera. But then I was like, “Hmm, I don’t know.” Actually the final thing was my employees saying, “Why are we doing this? This doesn’t seem like a way to have a good time,” type thing. 

MATT: That’s great that you had the kind of culture where people felt comfortable challenging that as well. 

STEPHEN: Yes, yes. I think it’s fair to say that we have a culture — We have a lot of very bright people who have a lot of opinions. And I like to believe that we have a company where what we are mostly interested in is finding people who can be productive in our environment, and they have very different personalities. Some of them, I think I at least, have the view that they pretty much couldn’t work anywhere else because they’re —  

MATT: [laughs] Unemployable.

STEPHEN: They have very unusual personality traits and poor internal politics skills and so on.

MATT: What makes them successful at Wolfram?

STEPHEN: That they do good work. That’s the thing that I —  

MATT: Part of good work is working with colleagues and the teamwork aspect.

STEPHEN: Yes, yes. But I think that the role of management is given who these people are, how do you fit them together with what we are trying to do in such a way that you take advantage of their good traits.

MATT: So to end the business thread, do you grow the employee base of the company along with the revenue or with your scope of what you’re trying to accomplish?

STEPHEN: Good question. We have been lucky enough, touch wood, that we have been profitable every year for 31 years now. That is achieved by a very simple process, which is, spend less than you make. Thankfully we have never had to have a big “Oh my gosh, the revenue is less than we expected, let’s let people—” No. We’ve fortunately never had that. Our general principle is we’ll pay Champaign, Illinois rates for a certain set of people. Other people, it will be based on where they are, but we’re never going to go above that. 

So that means when people wind up in San Francisco or New York, we’ll often lose them because we’re not going to pay the rates that people expect and need in those places. On the other hand, if they find some obscure place somewhere, they’re going to be doing really well because —  

MATT: I recommend Houston, where I’m based. Not too obscure and a very reasonable place to leave.

STEPHEN: Yes, we have quite a number of people in Texas. I think we may even have a couple people in Houston. I’d have to look at the map.

MATT: I read some really interesting research hypothesis around why geographic mobility has gone down in the United States. You would think people would move more for economic opportunity but it has actually gone down. And the conclusion of this was the blocker was two-income households. 

STEPHEN: Yes.

MATT: Where if one person were moving, and the sole breadwinner, you only have to find one job. And now you have to find two jobs in the new city, which is at least twice as hard.

STEPHEN: That’s interesting, yes.

MATT: But when one of the partners has no geographic attachments, you end up following. I just talked to a colleague who ended up in Copenhagen and he’s from — I forget where — some place very far from Copenhagen. He said, “Yeah, my wife got a research job and now we’re in Copenhagen for a few years.” 

STEPHEN: Yes, we find that all the time. There were some obscure ones. Like there’s one guy in our user interface team who’s been at the company a long time, but he said, “Well I’m going to go remote and I’m going to this island off the coast of Nicaragua because my wife is a primatologist and she is studying… What were they? Some kind of monkey-like creatures on this island. And he got a microwave link set up, and there he was, being perfectly productive.

MATT: Impressive.

STEPHEN: To me the focus is on — Can you be productive? Are you doing good stuff? And then where you live is your independent business, so to speak. There is a certain amount of complexity in scheduling things and meetings and so on when people are in all different time zones, but somehow that doesn’t end up being that horrifying.

MATT: Is there some sort of predetermined taxonomy or is it more of a free-form?

STEPHEN: It’s free-form. One of the things that is fun about my company is I think of us as a microcosm of what goes on, because we have people from the history PhDs who are actually doing history stuff for us, to the people who are doing — whether it’s graphic design or whether it’s some software engineering, server infrastructure thing. 

One of the things we’ve done — I don’t know how you’ve done this — but the company is pretty vertically integrated in the sense that we don’t outsource anything really. It’s all in-house graphic design, legal, this, that, and the other. Partly because we’ve got enough stuff going on that there’s not really a group that’s going to have nothing to do. And it also really, really helps to have, let’s say, designers who really know and understand our technology, and they’ve met customers of ours and they know the story. And plus some of the people in our design group become really good Wolfram Language programmers. 

MATT: Cool. Actually some of our best developers and architects started off as designers.

STEPHEN: Yes, I think it’s a really good field to start in. It’s funny, because I track where people come from and so on, and physics, for example, is good. For the techies, it’s a really good export field, so to speak, and I think graphic design is another one of these good export fields, where you learn a certain discipline of thinking to do good graphic design. 

For a while it seemed like UX was — we were pretty early in the hiring of official UX people and it seemed like that might be taking off more in that direction, but I think it’s a little bit merged with the graphic design. And I feel like sometimes the designers — they always have something to show for what they’ve done, in a sense, whereas UX is a little bit less clear. Somebody made this flow diagram or something but that turned into something different from what finally came out.

MATT: The visual communication helps a ton, right, for getting people on the same page?

STEPHEN: Yes. 

MATT: It’s one thing we’re trying to do more, is just draw something, even if you’re not an artist or a designer or anything, so you really are on the same page, literally, with what you’re trying to communicate.

STEPHEN: Yes. I don’t know in your geo-distributed setup, but we never use video conferencing, I mean really never, to the point where —  

MATT: It’s always screen sharing and voice?

STEPHEN: It’s just screen sharing and voice.

MATT: It’s mostly video actually, with us. And what was interesting to me observing it from the outside, is before Zoom, we had very few meetings because I felt like the process was so frustrating to everyone, we just didn’t do it. And Zoom spread like wildfire in our organization because there was just something to it that made it —  It worked just a bit better, it got over that threshold, whatever that uncanny valley was that kept us from using it before. And now I think we have too many meetings, perhaps. But video is a thing, and people think about their background and try to have good lighting. Good audio is really important to me personally.

STEPHEN: Yes. Good audio is very important to me. I am always complaining about that. 

MATT: I will send you a link to the Sennheiser headset we like. It’s USB and it’s only about $34. It’s become very standard.

STEPHEN: OK, I’d like that. Yes, we’ve spent lots of effort on headsets for people and complaining about people not having the right audio setup and so on. And I am glad to know that I’m not the only person who really cares about that.

MATT: It makes a huge difference. I’ll use this opportunity to tell people to check out your blog post. Was it “Seeking the Productive Life?”

STEPHEN: Yes.

MATT: On your WordPress-powered blog.

STEPHEN: Indeed.

MATT: Which is a very comprehensive view of your entire personal operating system and productivity, which I found — well, it’s impossible to summarize. And then two, we used this to point to [the fact] that you have started livestreaming many of your design meetings.

STEPHEN: Yes.

MATT: And so I could probably google “Wolfram livestream” or something?

STEPHEN: Probably, yes, right.

MATT: And so these actual internal meetings are now broadcasting publicly, which is pretty unique and fascinating.

STEPHEN: That is correct. This livestream meetings thing, I started doing it about a year and a half ago or something because I thought, these meetings are fascinating. It’s a shame for these things to just go off into the ether and nobody —  so I thought, let’s do this.

MATT: It’s mostly screens and then audio?

STEPHEN: Screens and audio, no people. We’ll get people who are both expert users of our product and often world experts in the particular thing that we are talking about. And they show up and they contribute useful things.

MATT: It’s interesting. You have a lot about your company which is very much like how open source works, but a lot of what you do is not open source, correct?

STEPHEN: That is correct.

MATT: There is a post I read about this while doing some research, 12 reasons — I think one of your colleagues wrote it — that Wolfram Language wasn’t open source. And one of them was, things like language design aren’t benefited from being more open, is how I interpreted one of them.

STEPHEN: Yes, probably, yes. I think — look, it’s a complicated thing because my goal is to be able to produce this intellectually valuable, long-term thing. And the question is, given the world as it is, what is the best way to do that. And we have built, back 33 years ago, when I started the company — it was like, OK, we’re going to sell pre-packaged software. And I didn’t know whether that industry would survive. I mean back at that time — 

MATT: It wasn’t clear, right? Piracy was huge. 

STEPHEN: Yes, piracy was a big problem. Another big problem was, what was the price point going to be for software? Because at that time there was Borland versus Microsoft. Borland was at $100, Microsoft was at $500 for typical software. And it’s like, who’s going to win in that space?

MATT: How much is Mathematica?

STEPHEN: Well it’s very complicated. [laughter] It ranges from —  

MATT: How much was it at the beginning?

STEPHEN: It was $495. But no, I think what we’ve done — it’s a thing I’ve thought about quite a bit — what is the right way to slice — We are trying to do a long-term, intellectually valuable thing, having something — maintaining that kind of coherence over a long period of time, I don’t know what the best way to do it is. I think we have found a pretty good scheme. Wolfram Alpha has been free from the beginning to use.

We recently introduced this thing, a free Wolfram engine for developers, which people seem to like. And the deal is, using it for development, it’s free, you can do whatever you want with it. But if your work product is what it is producing, if it is actually in production, that’s when you have to start paying something for it.

MATT: I think it’s interesting, you’re adopting some of the elements of what helps open source become ubiquitous, and some of the open things that, by the way, open source didn’t invent — they came from academia and many things before, in terms of the collaboration — and I think it’s very cool.

STEPHEN: An important thing for us is the alignment of where we make money versus who is actually getting value, who our real customers are. And I think some of the cracks that are happening in some of the areas of the technology industry — I think come from a lack of alignment between — who are the actual customers? Well the actual customers are advertisers, they are not the people who are — whatever else. And I think we have been both lucky in that our customer base is wonderful people we really like.

The thing that tended to happen though is these projects that — it starts open source and then there is some kind of bait-and-switch somewhere. And it just drives me crazy. We keep on —  

MATT: I totally agree. And that was the open-source model for a long time. We’re going to be open source but then hey, that open-source license is really scary, don’t use it, buy our proprietary license, or things like that.

STEPHEN: Right.

MATT: Or we’re going to put all the good, new stuff in this proprietary version of the license. 

STEPHEN: Right, right.

MATT: That’s why I want to talk more about open source at some point because, if you look at — They’re not always the best products, Wikipedia was not the best, WordPress in some ways you could say is not the best. Chromium engine — I don’t know if you saw the engine behind Chrome was just actually adopted by Internet Explorer.

STEPHEN: Yeah. 

MATT: So we’re getting a ubiquity and a de-facto standardization of a code base that becomes so useful.

STEPHEN: Right.

MATT: You could never force Microsoft and Google to say, “We’re going to do the same thing.” But they have, through their own personal utility maximization, have chosen to collaborate in this one area, which is really beautiful.

STEPHEN: That’s interesting. There are these different things, like, let people see the source, right? I don’t care if people see the source, that’s not the issue. I mean that’s not the point. Although we did have an interesting experience. 

So one thing happened because our products get used for lots of fancy, tech-y things. At the very beginning we would have the following sort of thing that would happen. Some mathematician would come up at a trade show and say, “How can I trust your stuff, I can’t see inside how everything works?” And I’d say, “Well how can we trust these papers you’re writing?” It’s kind of like, their mechanism for validity is peer review. Our mechanism for validity is software quality assurance, which is a lot better. 

MATT: I take it you have some opinions on peer review?

STEPHEN: Oh, it’s terrible. I think peer review is — I always thought it was broken, even when I was in the business, so to speak. My point of view was, if I have an original paper or idea, it’s going to be really tough to get it through a peer review process. 1986 was the last time I published a paper in an academic journal. I decided they were a bad idea and I wasn’t going to do it.

MATT: And now you have a blog, which is even better.

STEPHEN: Yes, the blog is — some of the things I write on the blog are quite academic. And it’s really interesting, I remember I was writing a piece about Ada Lovelace, actually, at the time of her 200th birthday celebration. And I happened to, at the last minute, I decided to go to England and go to some fancy celebration that was happening about it. 

And I was visiting some museum that has a bunch of her papers and so on, which I’d already got copies of most of. But the curator there was saying, who was used to academic stuff, was saying, “When do you think you’ll be publishing this?”, thinking the answer would be a year from now or something. And it’s like, well no, I’m going to publish it tomorrow morning before I get on a plane. Because you can write anything there. 

MATT: And you do.

STEPHEN: And I write some stuff that’s quite technical and some stuff that is quite product-oriented.

MATT: Back to that live-streaming of meetings. I think it’s great that you say the meetings are kind of like they were before you live-streamed. They’re not too performative or anything.

STEPHEN: Yes.

MATT: I’ll add something else to that, which is you said you’re a CEO for life, more or less, there is a lot of authority vested in you and this company, but it also seems simultaneously that people are comfortable with challenging you and presumably the other executives. What do you feel like you’ve done to foster that culture where there is a comfort, it sounds like, at many levels to challenge you very directly?

STEPHEN: Yes, it’s an interesting question. I suppose that I’m actually prepared to listen at some point. Some of these things get quite heated. It’s hardly as if — I don’t necessarily — I kind of know myself well enough to know by the time I’m getting heated, I don’t know what I’m talking about. That is the typical — and I will even say that because if I can explain myself, I’m just going to explain myself. And it’s always frustrating when people don’t speak up and don’t say —  

MATT: Do you do anything to encourage people who you might feel are hanging back a little in the meeting?

STEPHEN: Yes. I am enough of a people person. The fact is that having been running a company for 33 years, if I wasn’t a people person it would have driven me nuts, OK?

MATT: Or them away and there wouldn’t be a company. [laughs]

STEPHEN: Yes, yeah, right. I like people, I find people interesting. Sometimes I would say, more cynically I would say, after I’ve been managing people for 40-something years, and you might have thought you’ve seen every pathology that could possibly happen. But no, there is always a new one. At this point I just find it faintly amusing that — “Oh my gosh, another bizarre thing I’ve never seen before.”

And I see a large part of my role being that I’ve got all these talented people, I’ve got all of these projects we’d like to do, how do we match talented people with projects we want to do?

MATT: Do people feel like they’re moving around or is there some stability once they get onto a project?

STEPHEN: There is as much stability as they want, basically. There are people who have worked at the company for 20 years, and have never done management even though I can tell they have a good personality to do management. And finally we persuade them, you should do this, and they say, “Oh this is actually quite interesting.”

MATT: Is that more in your head or do you do any sort of testing or other objective ways to determine people’s strength or potential abilities?

STEPHEN: No, nothing, other than the Who Knows What database of just factual information. 

MATT: And does this all come from you or is this also the rest of your executive team?

STEPHEN: No, there is a bunch of people who have gotten experienced at doing this, I would say. When I look at org charts of companies I always —  

MATT: I love org charts.

STEPHEN: Yes, right. That was probably a decade ago, I was like “Oh, our org chart is such a mess.” For a long time, our org chart was classified because there were people, it was like, particularly one person who was with the company for a long time, and has now spun off doing related things, but who was an executive at the company and was always like, “We shouldn’t really tell people what all the weird reporting arrangements are.” I wasn’t a big believer in this but it wasn’t… 

But then, look at our org chart, and it seems messy in many ways. And then I was working — actually that was with Microsoft — and somebody who is actually now an even much more promoted executive at Microsoft, said to me, “We were trying to understand how it worked.” He said, “There’s this company on the outside that has reverse-engineered the Microsoft org chart, we just buy their stuff to understand what’s going on.”

MATT: That’s funny.

STEPHEN: Yes, right. So I get this thing and it’s a big foldout thing and it’s fascinating because it’s a huge mess. I mean, I don’t remember whether it’s still a mess but at that time it was a huge mess and you could see lots of historical stuff. And so after that I felt so much better about our org chart. Although, our org chart is now much cleaner, I would say.

MATT: It’s the map and the territory, right? Our org chart is currently clean but it’s not comprehensive, so there are some things that aren’t represented on the org chart, which sometimes a person is in two different places, that might be represented, but then they have informal authority in an area that we don’t try to demarcate necessarily. 

STEPHEN: Right.

MATT: We have had a lot of success, actually, removing everything compensation-related from the management structure. So there’s only a few, only the centralized HR deals with all that and everyone else just focuses on getting the job done and peer feedback and everything.

STEPHEN: One thing at our company, which was a long-time joke, was the claim there are more projects than people at the company. 

MATT: Yes, we have the same thing, wow. 

STEPHEN: It has been a running joke — can we actually inventory all the projects? Well now we’ve, thankfully — I’ve got this team together to just go and do that and it has been a good process actually.

MATT: Are you familiar with Marie Kondo?

STEPHEN: Sure.

MATT: You know her thing is you put all the stuff that is the same, like all the clothing, in one pile. It sounds like you’re doing that from an organizational point of view.

STEPHEN: Yes, yeah… 

MATT: You’re trying to get all that stuff together so you can sort it out.

STEPHEN: Right. I’d certainly like to apply software design methodologies to the way that we’re doing things. Look, the thing that we have done that I think has worked pretty well is we have pretty good project management, tradition, and infrastructure. And part of that is, I’ll come up with some crazy idea, actualizing that has to be flowed through the organization.

Now to be fair, I think I am probably — one of my less-bad traits is that I’ll come up with these ideas and then people will say, “How on earth are we going to actually do that?” And I will actually know, that is, if they don’t. It will be like, because I know enough about engineering and the whole technology stack, that I’ll be like, “Look, we can — some thing or other thing has to be authenticated here, and do this and that and the other, and I can actually dive down to a pretty high level of detail about how it should be done.

And I think part of my role is to explain why things aren’t impossible. And I see increasingly with a lot of projects we have done, the first response is, “That’s just impossible.” I’ll have some idea and it’s — and actually I am happy when people say that. When I’m not happy is when people say, “Oh sure, we’ll do it,” when I plainly know there is no way they can do it, it’s too hard. And so then I’m trying to figure out, “OK, so let’s see whether we can figure out how to do it.” 

I think the other thing that I find I do a lot of now is, we have all these projects connecting — I’ll be in some meeting and somebody will be talking about, “Oh, I’m doing this, this, and this,” and I’ll say, “Oh, you should talk to so-and-so because they’re doing something similar.” And we were doing stuff to do with external storage systems. We have this group that’s been doing database integration and a blockchain group, and they all have things to do with this external storage story, and that becomes part of the role — explaining, just knowing enough about what’s going on around the company.

MATT: And how in this — I’m curious from a software point of view — how does maintenance work in this structure?

STEPHEN: Well that’s a good question. First of all, a lot of things we do in the language are quite modular. There’s a function, it fits into the language, but it doesn’t have a lot of nasty, dangling interdependency. 

MATT: Gotcha.

STEPHEN: We’ve gotten a lot of experience and good systems for doing software quality assurance, and I think we are pretty good at doing that. Some of the QA we have to do is kind of hair-raising, like a lot of real-time things, which are always difficult, but even for Wolfram Alpha, there is — the natural language is a fundamentally non-modular thing. 

MATT: Yes.

STEPHEN: So the classic example is if you type in “50 cents,” you have money, if you type in “50 Cent,” you get the rapper as the default thing. What happens when there is another rapper who is called “30 Cent” or something? That’s a very non-modular thing, and you have to be able to deal with all those kinds of situations. But I think we have done pretty well at that.

What we tend to do are these big subsystems. They get swept through every some number of years, and then a lot of stuff gets — a lot of things that we’ll fix —  

MATT: Who decides to sweep through the system? Is it because a number of bugs accumulate? 

STEPHEN: No, it’s not as organized as that. That’s a good question. It ends up being the people who run those engineering teams. I have to say that I am pleased with their level of responsibility in the sense that we are going to rewrite a bunch of the UI stuff because it’s out of date.

MATT: On the converse side, sometimes I believe it’s easier to write code than read code.

STEPHEN: Yes.

MATT: And so you get sometimes new engineers on an area who want to rewrite it partially to understand it.

STEPHEN: That’s true.

MATT: So how do you keep the over-read factor?

STEPHEN: Yes, right. Well I push back on that and say, “Why are we doing this?” In fact, I was just doing that yesterday, a particular thing. It’s like, we can do this wonderful thing — why are we doing this? This is not an important feature, this is just not the time to do it.

MATT: Are there programs around learning and developments or ongoing training?

STEPHEN: The one constant is a lot of our development, most of our development is in our own language. But at this point, most of the people we hire know it. 

MATT: Before they get there?

STEPHEN: Yes, it’s kind of scary that the system is older than many of the employees. And they’re like, “Oh yeah, I started learning this when I was ten years old” type of thing. So that’s — 

MATT: I’ve started to have conversations like that in WordPress and it is very humbling.

STEPHEN: Yes, yes, right. For some areas I let different managers have different rules about how they set that up, but some people insist the person should come to an actual office for some number of months when they start to get —  

MATT: This is onboarding.

STEPHEN: Yes, right. And that seems to work well in some cases. And I don’t know whether it’s really necessary, I haven’t really — we haven’t done a —  

MATT: Would a prospective employee know what kind of team they’re joining?

STEPHEN: Yes.

MATT: Are you hiring for specific teams or are they generally open roles and you try to place people based on their — 

STEPHEN: We are placing people. But by the time they are actually joining, it’s pretty clear what they’re going to be doing, for sure. 

MATT: You’ll say, “Hey, you’ll need to come to Champaign for two months,” or something?

STEPHEN: Yes, right. sometimes we’re hiring people where it’s like, “When I finish my PhD I’ll come,” and they’ll start in some number of months and we’ll say, “Well we’ll have something interesting for you to do.”

MATT: By then.

STEPHEN: Yes right, yes.

MATT: Let’s say I’m a coder in Houston and I apply to Wolfram. What is my process like on the way to being hired, assuming I will get hired?

STEPHEN: That’s a good question, actually, I don’t — I have to say, I regret the fact that I don’t get to see most of the frontline applications, only some of the more senior ones. I used to look at a bunch of these things. Cover letters are, to me, a critical part of the story. I haven’t been reading them recently because I have — 

MATT: That’s why I don’t like applicant tracking systems, or form applications. I want to see how they email, what client they used, what fonts there are, how they formatted it. I want to see everything about the application as free-form as possible.

STEPHEN: Yes, right. What I find is that when I used to read these things a lot, the ones that were just, “Oh my god, I can’t believe this.” “I just graduated in computer science from this place and therefore I am qualified for whatever.” It’s like, no. And then there are other ones which say —  

MATT: There are some cover letters though that are such a good story, and you can get a sense for someone’s clarity of writing.

STEPHEN: Yes, yeah, right. Well, also some of the ones that are more fun are things like, “I’ve been reporting bugs in your software for six or seven years now, I want to come and help fix them,” type of thing. That’s kind of cool.

MATT: What are the characteristics that you feel particularly makes someone successful at Wolfram Research?

STEPHEN: A certain independence of mind, that they can think about — that they keep the thinking apparatus engaged at all times. Oh, yes, a very important one — no bullshit. That’s a — 

MATT: How do you detect that though?

STEPHEN: It’s really easy, I think. You just listen in the interview how people will say, “Oh, yes I know all about that process.” Well, I know a tiny bit. And sometimes —  

MATT: Some people can be more humble in their —  

STEPHEN: Right.

MATT: So interviews are very high-pressure. We do a lot of our interviewing on text, on a chat. 

STEPHEN: Oh that’s interesting.

MATT: And that’s partially because we found that there is a class of people for whom a real-time conversation like this can be incredibly intimidating. There’s an asymmetry as well. They’re hoping for a new job and they just don’t perform well in that situation. That looks like almost nothing else we do in most people’s daily work. The interview, it’s very artificial. But the text chat looks a lot like what an average developer might do most of the day.

STEPHEN: That’s interesting.

MATT: So it can allow people that kind of space to — it’s like a take-home test a little bit. They can take five minutes to respond to something, they can Google something, if they get really freaked out by the question, they can take a walk around the table.

STEPHEN: I have to say, in all the interviewing that I do, people sometimes come into it tense but I don’t think — I think if you’re doing interviewing right, the people aren’t that tense.

MATT: It’s probably an inherent power dynamic that is impossible for you, in particular, to remove.

STEPHEN: Maybe, maybe.

MATT: Well text removes that even more.

STEPHEN: Yes. I would say that at some level, if the people are sufficiently intimidated, that’s probably not a great indicator, because the fact is, in our company, there are a bunch of strong opinions and people will express themselves. And if somebody is like, “Oh no, I can’t deal with that,” that probably isn’t a great indicator. 

I have to say, it’s a different thing with more senior folk, like business people and things like that. That’s a horrifying world of interviewing, for me at least. Because people who have, who are used to a very polished presentation, it’s just so difficult to find out who is the actual person here. 

MATT: How do you balance that pattern matching? Not leading the confirmation bias or where the company might need to evolve, which might be different from where it has been in the past?

STEPHEN: I’m a guy who likes new stuff, so that helps me be more change-oriented. I have to say that by the time it’s working smoothly, I’m not the person to be dealing with that. I have for myself and my personal life, I have endless systems that I have developed and they work, but also sometimes they stop working and then I’m like, “Oh, this doesn’t work anymore, I’m going to change it.” 

For example, it could be the case that the things that I like and that resonate with me and that are the directions that I think of going are just not the ones the world happens to be keen on. A couple years ago I was like, “Let’s look at VR and AR.” And it’s like, well, I have a bunch of long-term people at the company, and they said, “You told us that in the early 1990s.”

MATT: That’s funny.

STEPHEN: What a bust that was at that time. You’re going to have to do better this time to convince us. And I have to say, I couldn’t. I couldn’t really convince them. Or IoT is another area where we’ve done a bunch of stuff, a bunch of interesting things, but it hasn’t quite taken off the way that I think some people thought it would.

This question of, when you’re the CEO, when do you fire yourself, type thing, and do you change, or is the thing going in a direction that you just don’t want to change it? 

MATT: And your name is in the company, so how does that happen?

STEPHEN: Yes, right.

MATT: Is it just “research” at that point? 

STEPHEN: Right. That’s an interesting issue. I was thinking —  

MATT: We joke Automattic would be just “Auto-ic.” 

STEPHEN: Right, right. I’ve been thinking of this. I was thinking at one time if I had a club of people who had named their companies after themselves. And you’ll be a partial member, right?

MATT: Thank you. Well we luckily have, I think, 17 other Matts at the company, so it could keep going without me.

STEPHEN: OK, OK. But I think —  

MATT: Yes, I do joke — the egotistical founder, we always slip our name in. I want to ask two things as we wrap up. You have a lot of trust, it sounds like, which just allows this very candid communication, candor between folks. Do you have something like the meetups that we’re doing here? 

STEPHEN: Yes, it’s not quite as formal. Once a year we have a technology conference. Users come, they have a good time, they get to meet a bunch of our employees. The employees come, they have a good time, they get to meet a bunch of our users. 

MATT: Cool. Well after all this time, would you consider management or running a company computationally reducible?

STEPHEN: [laughs] That is a good question. This is one of the embarrassing things about people who like to think they’ve invented paradigms for thinking about stuff. The question is, “Can you live your own paradigm?” And it’s often the case in these things where I can see something developing at the company — I’ve been doing this a long time so I know how this story ends. 

From the point of view of science and technology, there are things we’ve invented, I’ve invented. I could be very worried. Is the world ever going to pay attention to this, is the world ever going to care? Maybe I’m just too arrogant, but the fact is, I just know it’s going to go that way. This thing about computational language and the importance of having a rich language which can express computational thoughts, this is inexorable. This is going to be really important. I don’t know how long it will take the world to realize how important that is.

MATT: It’s not if, it’s when?

STEPHEN: Yes, yes. 

MATT: Well that’s a good place to wrap up. Stephen, thank you so much. This has been an endlessly fascinating discussion and I’m looking forward to continuing it over dinner.

STEPHEN: Sounds good. 

MATT: This has been Distributed with Matt Mullenweg and we’ll see you next time.

MATT: That was Stephen Wolfram. You can find him on Twitter at @stephen_wolfram. That’s Stephen with a PH, underscore, Wolfram — W-O-L-F-R-A-M. He also has an awesome blog, if you just google his name and “blog.” It’s powered by WordPress of course, and it’s really good.

Stephen says that he set out to build a company that would, quote, “allow him to build the tools to do what he wanted to do.” And by that he means working on projects that he calls “intellectually valuable.” It’s easy for CEOs to come up with lofty mission statements, but very few actually follow through. I’m inspired by Stephen’s steadfast commitment to intellectually valuable work and the organizational freedom that has allowed him to pursue it across three decades — and hopefully for many more to come. 

Next time on the Distributed podcast, we’ll be talking to Taso Du Val, the CEO of Toptal, a freelancer network where employers can access a highly curated pool of remote contractors. Toptal itself is fully distributed, and they’re trying to convince blue-chip companies to integrate remote talent onto their teams, so I’m excited to talk about how this could help usher in a distributed future.

Thanks for joining us, and see you next time. 

Read more about Sonal Gupta in “Welcome to the Chaos.”

Sonal Gupta leads Automattic’s Other Bets division, a team that builds products that aren’t yet core to Automattic’s business, but keep the company innovating and pushing it to explore new territory. In this episode, Sonal and our host Matt Mullenweg talk about how important communication is in the organized chaos of a fully distributed company.

The full episode transcript is below.

***

MATT MULLENWEG: Howdy howdy. I’m Matt Mullenweg, the CEO of Automattic, and the co-founder of WordPress. Automattic is the company that makes WordPress.com and a bunch of other things. At Automattic we have a division called Other Bets, which encompasses a host of experimental projects that aren’t directly related to our core business. When we started thinking about this department, I knew we needed a renaissance person to lead it — with a background in legal, finance, and entrepreneurship, Sonal Gupta is just such a person.

Sonal’s been with the company for coming up on three years, and I wanted to get some time on the calendar to talk to her about what made her want to work for a distributed company, what she likes about it, and what she finds challenging. 

Alright, let’s get started with Sonal. 

MATT: Today we’re going to go inside a company I know a little bit more about — Automattic, which is a company I founded in 2005. Today, Automattic has over 850 employees working from 68 countries. 

So to understand better how Automattic works, I’m joined by one of my colleagues, Sonal Gupta. Thank you so much for joining today, Sonal.

SONAL GUPTA: Thanks for having me.

MATT: She is the lead for what we call the Other Bets Division, a name we borrowed a little shamelessly from Alphabet, which oversees a number of different emerging businesses, including our latest bet, which is focused on tools that power our distributed work model, Happy.tools. 

Sonal is both a tech founder and a lawyer. She joined Automattic two years ago as a legal counsel after a successful run as cofounder of Rank & Style. And Sonal, you’ve also been named as one of Fast Company’s 100 Most Creative People. So when you joined Automattic, it was your first distributed work company. What made you want to apply for it?

SONAL: Yes, actually the distributed nature and culture of Automattic was one of the things that really drew me to it in the first place. I was really intrigued and loved how open and transparent everything was and the amount of autonomy Automattic places on its employees. 

I had had all sorts of experiences with different offices as a corporate lawyer for a big part of my career. I worked in a big corporate office here in New York City where I had my own —  

MATT: How big?

SONAL: 500 employees.

MATT: Wow.

SONAL: Not huge but for one office it was pretty big. The office itself was nice, but the expectations around face time and just being in the office just in case a client might need you, those types of expectations made it a little bit difficult to keep up that kind of lifestyle. 

I have also had other different types of office experiences. I have worked in open plan offices, I have worked in a cubicle at a bank, I have also done the co-working space at WeWork. So my experience in offices really runs the gamut. My two years at Automattic [has been] definitely the best fit in terms of the way that I work, the way that makes me most productive, and overall life/work balance. 

MATT: So one question that comes up sometimes is, “What’s the first day?” There’s no desk you go to or computer. What was your onboarding like?

SONAL: Well it’s funny because you start your first day and you’re sitting in your living room and your friends or family say to you, “Do you really have a job?” [laughter] The first day at Automattic was great. Automattic requires every employee to do a two-week support rotation so that everybody can understand the product and how customers see our products.

MATT: You log on that first day, you’re in your living room, you’ve got a laptop. What was your first impression?

SONAL: I think my first day I thought that there would be more video chats but all your onboarding is done — 

MATT: All text.

SONAL: All in text. So that’s — 

MATT: Were you paired with someone? How does it work? I haven’t been onboarded in a really long time.

SONAL: Yes you’re paired with a buddy — mentor — for your support rotation. You’re trained completely on Slack with a group of others who are also starting that day.

MATT: And going from law to doing customer support, what was that like?

SONAL: It was interesting. I did interact with our customers. I hadn’t really experienced anything like that. 

MATT: One thing people get on the first day is — internally to Automattic we have something called the Field Guide, basically our internal handbook, but it’s a WordPress blog so anyone can edit a set of pages. There is a headline on the Field Guide that says “Welcome To the Chaos.” What did you think when you saw that?

SONAL: Seeing that just gives you comfort, immediately. Because it is overwhelming. You’re getting pinged from every direction. But as soon as you learn to embrace the chaos rather than resisting it, it makes it so much easier to understand Automattic’s culture.

MATT: What does it mean to embrace the chaos?

SONAL: To embrace the chaos to me means just surrendering to it and understanding that there is just going to be a barrage of information coming at you from all angles and it will take a little time to have a process in place, but you’re not expected to just get it immediately.

MATT: One of the things that I’ve always thought is —  recovering lawyers or attorneys — you write a lot in school, you read a lot, you are consuming and writing massive amounts compared to almost any other modern-day trade or industry. Automattic has a basis of a lot of written communication. Were there any things that you learned as you were training to be a lawyer that helped you in that, or that you found made you better able to consume and produce written stuff?

SONAL:  Yes, absolutely. Being successful at a company like Automattic — you have to be able to communicate effectively via text. As you said, we’re using all different kinds of messaging and internal blogs in order to communicate with the entire company. So I think my legal background was really helpful in being able to convey messages and information to people in a very clear and succinct way.

MATT: How many hours did you work in a given week before versus now? Did you burn the midnight oil in the corporate job?

SONAL: Oh yeah, definitely. I had times where I was working overnight or till four in the morning, but there are times at a law firm where you have downtime too. I think at Automattic, I wouldn’t say that overall I work that much less but I just work in a way that really works with my schedule and my life. So that is just something that is really important to me.

MATT: What’s an example of you using that?

SONAL: We use Slack and internal blogs for communication and it’s all async. While I try to get back to my colleagues or external partners as soon as I can, there is an understanding that we’re working with people in all different time zones around the world and you might not be working the exact hours, or maybe I take off three hours in the day and make it up later in the night. However I want to make my schedule is allowed.

MATT: You joined as a legal counsel and you made the switch to running a division. Automattic has four divisions; you run one of them. Tell us about Other Bets. How many people, what does it do, etcetera?

SONAL: We develop or acquire products that fall into three categories — things that we need to exist for Automattic’s operations, things that we build as experiments or that are useful tools for our community, and things that have the potential for substantial revenue growth. A lot of our products cross multiple categories. We are currently 40 people in the division, spread across six different teams.

MATT: And I think part of the design goal of Other Bets is that we want about five percent of the company always working on the future.

SONAL: Yes, exactly.

MATT: Taking the thing that could be the next WordPress, could be the next Jetpack, could be the next WooCommerce, going from zero to one is really, really hard, and it’s different than going from 100 million to 120 million. We don’t disclose revenue, but we can say that Other Bets is about 10% of the revenue at Automattic, which is now starting to be quite substantial.

SONAL: Absolutely.

MATT: Tell us about some of the products.

SONAL: Well we’ve got about 20 products in the portfolio, not all actively developed at the moment. Some of our products are Crowdsignal, which is a poll and surveys platform.

MATT: Competes with Survey Monkey maybe?

SONAL: Exactly. And we’ve got our new suite of products, Happy Tools. Our ads business is also part of the portfolio.

MATT: One of my favorites is actually Simplenote. It is a simple notes app, and it runs on Android, iOS, Mac desktop, Windows, everything. It’s just ultra- fast synchronization of super clean notes. A lot of other notes apps become not that simple over time but we have managed to keep this one pretty lean and mean.

SONAL: That’s correct. So Simplenote is one that we’re constantly building and improving.

MATT: Let’s talk about communication. You have 40 people, how many time zones does that generally span?

SONAL: We work with people on both coasts in the U.S., a ton of people in Europe, and a couple people in Asia.

MATT: One of the things that’s interesting is, people think of distributed as being location-based. What do you think is the key to synchronous versus asynchronous communication? What can make that asynchronous collaboration productive?

SONAL: The fact that we’re in so many different time zones and people are working at different hours, you can pass the baton to the next person, especially on the development side. So if you have somebody working in the U.S. and then they go to bed at night when somebody in Asia wakes up, it makes it very easy and seamless to just keep continuous work on different projects.

MATT: Do the teams have regular meetings? How do they work?

SONAL: The teams do have regular meetings. Usually they use video chat, using Zoom. For teams with people in different time zones, they just try to find a time that really works for everyone. Sometimes they also communicate via Slack. We also communicate via our internal blogs, which we call P2s. Between the three, there is generally very seamless communication.

MATT: When do you use a Zoom, a Slack, a P2, what do you use these for?

SONAL: For Slack I think it’s great for conversations with one or a smaller group of people where you’re just trying to stay on the same page in real-time communication. Our internal blogs are really useful for keeping the entire company up to date on our progress or different updates. They’re really helpful for being able to search our entire database of P2 posts so anyone coming to the company in the future can always get all the backstory on a specific conversation or product.

MATT: If you met with a partner, you would post notes from that to P2 or to Slack?

SONAL: If I met with a partner, I would post notes to a P2 and just make sure that everybody at Automattic who needs that information can easily access it. If I’m making a quick decision about something and I just needed somebody’s input, I would probably use Slack. I have one-on-ones with each of my direct reports on a weekly basis and for those I generally use Zoom video chat. I really do value in-person or face-to-face communication so I think Zoom helps fill that gap.

MATT: It’s funny because you’ve used face-to-face and Zoom a little interchangeably and really that’s screen-to-screen, right?

SONAL: That’s true.

MATT: And video communication is obviously higher bandwidth. So you get a lot of value from that. When do you get together in person with people?

SONAL: Most of the teams meet up at least once or twice a year on their own and then there is also an all-company Grand Meetup every year where the entire company gets together. I, as a division lead, try to meet with each of the teams as much as I can. So I’m generally on the road.

MATT: So you have six teams meeting twice a year. That’s 12 meetups. Do you go to a lot of those?

SONAL: I wouldn’t say that I go to every single meetup but I try to make sure that I get some time with everyone on my teams at least once a year, and then at the Grand Meetup as well. So between team meetups and conferences, I’m probably on the road once a month.

MATT: What makes a great meetup?

SONAL: If a team comes up with a meetup project that is something they can complete in a week, I think that always feels really satisfying. Or if they’re just in the middle of developing a product and they can come together and make some progress on that, I think that always feels really fulfilling. And then the team bonding is a really big part of it too. They’re all working together, every day, all year long, and they get about two to three weeks of in-person time together. So most people find it really valuable. That catching up over dinner and really getting to know each other is an important part.

MATT: A common question that managers at distributed companies could ask is how do you know your teams are working?

SONAL: I’d say that posting on our internal P2s is one way that you can have a sense of how much people are working, how many ideas they’re sharing, what kind of meetings they’re having. So I think we do put some value on how much people are posting but other than that… 

Personally, I’m not a micromanager. I like to trust people and give them autonomy. But I keep in touch with them very regularly and I think it becomes clear pretty quickly if somebody is not doing work. We look at performance, and we look at communication at a distributed company. Communication is oxygen. So it’s just really important that people are constantly communicating. I think we probably veer closer to over-communication. In some ways you have to make sure you know how to sift through all the different communications coming your way but I think it’s an effective way of understanding what people are working on.

MATT: Think of your best team — you don’t have to tell me which one it is — but what are some things that they do that you think makes them very effective?

SONAL: I think my best teams are great at communicating via P2 and having roadmaps and plans in place, and making sure that they’re meeting their plans or, if not, updating me. 

MATT: So Sonal, you do a lot of recruiting and hiring for your division. How does that change when you’re hiring from everywhere in the world, versus when you’ve hired for startups or companies in the past, and how does that interview process work?

SONAL: It’s very unique. The benefit of hiring at a distributed company is you have access to a global pool of talent, which allows you to bring in the most diverse qualified candidates. As far as the interview process — it is quite unique. Some teams hire completely through text communication without ever hearing a candidate’s voice. I personally haven’t done that yet but I generally interview on the phone or via Zoom or sometimes if a candidate is local I’ll meet them in person.

Everybody we hire, we have them go through a trial project process first, which usually lasts about a month. That really helps us figure out if the candidate is a good fit and it also helps the candidate figure out if a distributed culture works for them.

MATT: So like a two-way evaluation?

SONAL: Exactly.

MATT: Thank you very much, Sonal, for joining us today on the Distributed podcast. If you want to learn more about Happy Tools you can sign up for a demo of Happy Schedule at Happy.tools.

SONAL: Thank you so much for having me, it’s been great to be here.

MATT: That was Sonal Gupta. 

Automattic has grown so much these past few years, and at over 950 employees, it’s not always easy for me to get a ground-level perspective of what’s going on in the various parts of the company. It’s great to be able to catch up with people like Sonal, who keep me up-to-date about all the exciting projects going on, and about how our distributed work model complements those projects. Thank you for joining us, and see you next time.

Read more about Scott Berkun in “Observe, Don’t Surveil: Managing Distributed Teams with Respect.”

Scott Berkun wrote the book on distributed teams. Literally. He spent a couple of years at Automattic and wrote about his experience as a manager in a distributed company. In this episode, Scott talks about that experience, discusses how things have changed since, and explains how today’s managers can cultivate a shared vision in a distributed team.

The full episode transcript is below.

***

Matt Mullenweg: I want for you to imagine that you’ve been hired as a manager at a scrappy startup where there are no meetings, no hierarchy — not even an office. How do you make people feel like they’re part of a team? How do you brainstorm, and how do you make sure the work’s getting done? Is it possible to cultivate a shared vision, structure, and goals by only meeting in person twice a year? 

That’s what Scott Berkun faced nine years ago, when I hired him to join a little company called Automattic, which is the parent company of WordPress.com, which I founded in 2005. 

As you know from listening to this podcast, Automattic is fully distributed, with no central office and more than 900 employees working from 68 countries. When Scott joined us, we were quite a bit smaller, we were using IRC instead of Slack, and there was a lot that we were still figuring out.

Scott wrote a book about his experience at Automattic called The Year Without Pants, and since then he’s written a whole bunch of books about management, culture, and how we work. Today he’s a sought-after speaker on creativity and innovation.

I caught up with Scott in Seattle to talk about his experience at Automattic, and everything he’s learned since then. Has the future of work panned out like we first imagined it?

Matt: We used to work together, actually. 

SCOTT BERKUN: We did used to work together. I used to work for you. [laughs]

Matt: Well let’s talk a little bit about how that happened, because that was an interesting arc in the story.

Scott: Yes. That was probably 2009 that you asked me to come to an Automattic Grand Meetup and you wanted me to advise on the team or lack of team structure at the company at the time. That was the first time that we officially were working together. 

Matt: That’s an intriguing hook.

Scott: Yes.

Matt: And I guess that was a point when Automattic was totally flat, right? 

Scott: Yes.

Matt: It was like 50 or 60 people all reporting to me. I don’t know how that worked, actually.

Scott: That’s right, yes. [laughs] 

Matt: I don’t remember.

Scott: We talked a few months later about me joining Automattic as a lead of one of the newly formed teams at the company.

Matt: Before that you had been at Microsoft for a while?

Scott: I was a team lead, a project manager guy for about nine years there and I wrote a book about it, which is — probably how we first knew of each other is that you were on my mailing list that was about project management.

Matt: Oh was that the Art and Science — the Project…

Scott: Yes. That’s how we first titled the book. And then when WordPress launched I used it for my blog and that’s how we got to know each other.

Matt: Can we plug that book really quick? What’s the new title?

Scott: The title is Making Things happen. That’s the title of the book now.

Matt: I highly recommend it. That’s the one with the matches on the cover, right?

Scott: That’s right.

Matt: I really enjoyed that book.

Scott: But that was the beginning of my full-time remote work experience was working for you at Automattic. And I remember one of my biggest reasons for wanting to do it was that it very clear in your mind and in my mind that this was an experiment. Can we bring this experienced manager from a traditional company into a company like Automattic that has all these special things — being remote is one of them — but the high autonomy that every individual employee had — continuous deployment, was another. And then the notion of teams itself was an experiment. And then there was also this other notion that you knew that I was going to write a book about this, which was this other curveball to the whole thing.

Matt: Yeah.

Scott: And that combination of experiments — I love the word experiment, and when you used that word, I felt like no matter how this went, it was going to go well. For one of us, at least.  [laughter]

Matt: Yeah, sometimes those book documentary projects don’t go as well.

Scott: No. The distributed work element wasn’t my greatest concern. I was worried about that but I was more worried about — do my skills as a manager in a traditional company where it’s an open office — you see people everyday. Could those skills transfer well to distributed work and to a far more autonomous culture in terms of the individual’s relationship to their work — how much control they had. I was more concerned about those things than distributed work. 

Matt: I think this is a big concern of a lot of managers who have worked one way their whole career and then might be thinking about joining or starting or working in a distributed fashion. What did you see your superpowers as when you were in these in-person cultures?

Scott: I don’t know that I ever thought I had a superpower. I thought — 

Matt: Well you’re a modest guy so let’s call it “medium-powers,” that made you effective at what you were doing.

Scott: I thought that, and I still think this, that most managers are really not very good at managing. Most people you talk to, when they come home from work, they’re not that happy about how well they’ve been managed — they have complaints. And that may extend out to the way the team is organized or the way the goals for their product has been set. 

I thought that I was a good team manager in that I remembered all of my bad experiences as an employee and I tried to work really hard not to repeat those mistakes. And I gave a lot of autonomy to employees because I was one of those employees who liked a lot of control. Once I’ve earned some trust I wanted to be able to run and go at full speed. And the best managers I had are ones who are comfortable giving me that much control. And I tried to rely on that as a strength coming to Automattic. Because everyone was already independent. I have to start out by saying I may not actually add any value at all. I need to observe first to see how things are going before I have any reason to change anything. 

And that’s a common mistake that new managers make everywhere, that they come in and they’ve got this new salary, this new job title, and it kicks their ego in and now it’s about them — How am I going to change the team, how am I going to change the organization? But you don’t know anything, you don’t know these people, you don’t know what their strengths or weaknesses are, you have no data. 

So the best thing you can do — and this comes up in the book that that was what my strategy was for two months — I’m just a note taker. When we have meetings, I’m just going to take notes. I’m going to observe, I’m going to reflect back. And then little by little, once I have something useful to say, I’ll put it into — well it was IRC then but it’d be Slack now — little by little I’ll just try to show, A, I’m not stupid, B, I’m not trying to get in your way, and C, I may actually have some insight that will help you be more productive or successful or happier. And you have to earn that even if you’re the most senior person on the team or the company or whatever.

Matt: How do those meetings happen?

Scott: Well obviously there weren’t teams yet so there were no meetings. [laughter] So what we agreed to do was — 

Matt: Were those Skype calls? 

Scott: It was all text.

Matt: Everyone would be there at the same time, once a week?

Scott: Yeah. And we would chat about whatever everyone was working on. And it started off really short and little by little we added more structure, then we moved to Skype and then eventually the big breakthrough was we switched to audio! Woohoo! It was a big deal because everyone was fully paying attention.

Matt: We’ve had different experiences on audio meetings.

Scott: Yes…

Matt: Just to define some of those terms…

Scott: Yeah.

Matt: IRC is a text-only chat. 

Scott: Correct.

Matt: Think of it like Slack but with a really old school version, like almost terminal-like interface.

Scott: Old school, yes, old school Slack.

Matt: Skype is a messaging platform plus voice.

Scott: Yup.

Matt: And is that what you did the voice meetings on?

Scott: Yeah. We agreed we’d keep the meetings really short but every communication tool is good for some things and bad for others. And text has the advantage that you have time to think but the downside is that written language takes away a lot of data. You can’t hear someone’s inflection in their voice, or pick up on how loud or quiet they are. There’s a lot of data that you lose. 

And having a moment every week where we were on audio, even if it was just for five minutes or ten minutes, emotionally, in terms of your relationship, in terms of understanding people’s nuances and sense of humor, their sarcasm — you could only get that through audio. And you don’t need that much, you don’t need to have two-hour meetings, but ten minutes a week to hear everyone, what they’re talking about, what they’re excited about — you get more data. And I think that helped us throughout the rest of the week.

Matt: That was enough for you to get what you needed to be an effective manager to this team?

Scott: That was enough to help prove that I had some value. Because people would leave those meetings when they were run well saying “Yeah that took 25 minutes but now I understand what Andy is working on, and I see now that’s going to help me later.” That was 25 good minutes as opposed to the typical way people feel about most meetings, which is [that] it’s about other people, it’s all just FYI, stuff that doesn’t go anywhere and it seems that the person running the meeting cares a lot about having them, even though no one else really is engaged. 

And then little by little it became natural for the team to look to me to set the goals and to help decide what features should be next or what things should be built. But you can’t do that as a leader without having some forum for those things to happen. And that’s what the weekly meeting was for us.

Matt: Is that how you saw managers come up in Microsoft as well or was this a unique approach you created for this opportunity?

Scott: I saw a wide range of styles at Microsoft. And this was more like the style that I preferred. I wanted to start off by trusting everyone and extending trust before I ask them to trust me. That’s just good —  

Matt: That’s a really powerful concept, yeah. 

Scott: That’s good relationship management. But I knew there has to be cadence. That’s the fancy word. There has to be a rhythm. If you’re on a team there’s a rhythm. You think of people who are competitive rowers, and there’s that person at the front of the boat who’s just — their job is just to yell out the rhythm, that’s all that they’re doing, the coxswain, right?

Matt: Yeah. 

Scott: They’re taking up weight on the boat simply to be the person who’s controlling the rhythm. And any team, even if people are working individually for the most part but there’s some things that overlap, someone has to be setting the rhythm for the week, the rhythm for the month, and to help people set their own rhythm for the day. And that’s what I thought my job was.

Matt: One thing I hear a lot about people who have had a lot of experience in a physical office is they get so much value from the kind of drop-in or walking around because you get — what you said you get with just a little bit of audio is an even higher bandwidth, right? If we go text, a little bit, audio better, video more — you can see faces — and then in person. Let’s call that the best. How do you deal with not having that?

Scott: All the claims people make about serendipity, you’ll lose all the serendipity of meeting people in the hallway or — you can replicate all that. That’s what the group chat rooms are for where you jump in and you’re bored and you see all the other people who are procrastinating on something. You don’t see them but you can chat with them. There’s randomness and surprise that can happen in any group situation. 

And all the one-on-one direct, more intimate communication, you have now fifty different tools to do that. You can send someone a private text message. “Hey, it seemed like you were upset in that meeting, should we talk?” Or you can make a Skype call. You have all of these tools to make the equivalent of what I would do at Microsoft, which is to go down to someone’s office and say “Hey, can I talk to you?” and close the door.

Matt: What about when that trust gets broken [and] someone doesn’t follow up on what they say they’re going to do? How does your approach there vary when you were an in-person manager versus being a distributed one?

Scott: I really have become a universalist about this, that as the manager — not even the manager — as a person, if someone has made a commitment to me and they’re not honoring it, part of my first thing to do is check in. “Hey, how’s it going, are you still on track for this thing on Friday?” I’m just checking, is my sense of the world in line with your sense of the world? If you do that periodically, especially when you don’t see them posting on Slack or giving any visible — you have no passive indicators that they’re following up on this…

Matt: So is quietness a warning flag?

Scott: It is a warning. And this is one of the things that I learned from you about Automattic was that if you don’t make your work visible it’s invisible. No one can see it. And if you’re not over — what feels at first like over-sharing — or making sure that your code commits show up in the team channel, [or] whatever you’ve agreed on, then that puts someone who is the manager and the responsibility now going, “Well that person’s been quiet for four days, I have to reach out.”

So my first thing is just to check in. Do we still have the same expectations and view of the world? Yes. That sets me up then to come back two days later and go “Hey, we talked a couple days ago, we have a problem here because if you don’t get this done then Sally can’t get her thing done and now it’s going to cascade. So what’s going on?”

90 percent of the time, there is a reason. “Oh, this other issue came up that was more important, I forgot to mention it to you.” I’m like, “OK, great, now I understand, I can recalibrate.” But someone has to be that check-in maintainer that is driven by whoever is in the leadership role. The hard part is when you check in on someone and they keep — there’s something broken still. They’re not getting their work done, they’re frustrated —  

Matt: Or there are broken things in the past. It was due on Friday and now it’s Tuesday.

Scott: Right. You really want to avoid having deep, personal conflict conversations over text.

Matt: Why? It seems so efficient.

Scott: It’s efficient until it’s only making things worse.

Matt: Ping, Berkun. 

Scott: [laughs] It’s what I mentioned before about what you lose, that you don’t get the nuance that is so important to empathizing and understanding what someone is trying to say. And if I have an employee who [has] some issue that’s going on that’s personal that’s got nothing to do with work, they’re less likely to type that in. 

But if I can get them on the phone and they hear my voice, and I can offer them my true empathy for — “I want you to do well, my job is to see you do well.” They get that empathy. Our brains respond to that more directly through voice and eye contact and facial expression. They’re more likely to respond back and share a little bit more about what’s really going on, which could turn out to be something simple, that the way that I assign work or the way that I make decisions bothers them in some way, but I didn’t know that. And they were afraid to offer that to me before.

Matt: So you created that safe space for that to be communicated.

Scott: Yes. I also think that even if you don’t agree with my point about intimacy, I think that every medium has strengths and weaknesses. And just by switching the medium it changes now what the strengths and weaknesses are going to be. To switch from Slack to SMS, although they both seem like text, there are subtle differences in the way people think and translate what’s in their head into communication. And so whenever I am stuck, I will always try to — and I feel like I don’t really know what’s going on here — try to switch the medium. The one that I always feel is the go-to one if I’m confused is voice. And often it’s faster.

Matt: I think that’s great advice and it’s a cool feature of the new tools, like Slack. They have audio built in so you can initiate a call right there. 

Scott: I have this experience with my friends. We’ll be going back and forth on SMS on something we’re not agreeing about and I know from all my experience at Automattic, I know that sometimes a 30-second phone call — 

Matt: Would fix everything.

Scott: Instead of a 20-minute — yes, we are asynchronous, I’m half watching TV while I’m doing it. But it is 20 minutes of time spent arguing about something that’s a nuance that would be completely obvious if we spoke on the phone for 30 seconds.

Matt: It was interesting, we just had a leadership summit at Automattic. It was a training one, and we decided that the focus for the week would actually be feedback. And in my mind going in, it was more about how to give good feedback, some of what we just talked about. But the facilitators, who were quite good, ended up focusing probably the bulk of it on receiving feedback. Let’s say you’re on the other side of things and you’re getting some feedback over text or something like that, what have you found works well or poorly for that?

Scott: I think that you have to start from separating out your personal identity with the work that you’ve done. 

Matt: Hmm. What does that mean? 

Scott: Well I’m a writer, so that’s the easiest place to start. I’m a writer, I write books. And people write reviews of books and a lot of them are really mean. Making Things Happen has a two star review on Amazon where someone says it was about as useful as a piece of toilet paper or something like that.

Matt: By the way, toilet paper is super useful.

Scott: It is super useful. [laughter] It’s all context-dependent though, right?

Matt: It’s interesting though, every author I know has this where at some point, even if they know they shouldn’t, they’ve read the bad reviews and they can usually quote it word for word.

Scott: Yeah. Oh yeah.

Matt: But maybe you can also quote a really good review but they typically don’t have that same vividness to the probably 10 times more good reviews that it’s gotten.

Scott: Yeah. I read every review. 

Matt: Yeah?

Scott: I think every review… not all the GoodReads ones but every Amazon review, every magazine review, and I feel like that’s part of my job. So I write a book and I do work knowing that there are going to be people who have valid criticisms of what I have made. And it doesn’t necessarily mean that what I did was bad, it just means that there’s many ways to decide what good is. That’s part of the job. 

And I feel like that’s part of the job as a manager, that’s part of the job as a developer, that’s part of the job as a designer. You are making stuff and putting it out into the world. That’s what I mean by splitting out my personal identity as Scott from “I made some thing that someone might not like”, or in the management case, “I made a decision that someone really is upset about.” 

Matt: So if I were to rephrase that — you created something that someone thought was worthy of two stars but that does not mean you, Scott Berkun, are a two-star person.

Scott:  Correct. I might be a two-star person but not just because of — 

Matt: Of this one review.

Scott: Right. Not just because of that book that I wrote or a thing that I did.

Matt: Or a thousand two-star reviews, ya know?

Scott: Sure, yeah.

Matt: That sounds hard though. You even started with saying, “I am a writer.”

Scott: That’s why feedback is hard because we, especially people who are passionate about their work, they don’t have much psychological separation between their identity as a worker and their identity as a human being, and that is a kind of maturity that you need to have. 

The helpful thing [is], I have a curious mind to ask clarifying questions. I’m not going to defend anything. I’m going to run with the assumption that they are correct. There’s something flawed in the decision that I made. But I have to be an investigator now. I have to — “OK, when you say this, do you mean that or that? When you say that you thought the decision was unfair, did you mean it was unfair just to you or to the team or to — ” I have to go into that —  

Matt: That’s a tough one because it can feel aggressive.

Scott: Yes.

Matt: Because on the receiving end it’s like, “Oh I’m doing all this extra work to justify my feedback I’m giving you.”

Scott: Yes. I think you’re pointing out how much trust is required to be a good leader, that I have to somehow convince someone who thinks I have done a lousy job that I genuinely want to learn more about why they feel that way and how they think about it. They have to trust me and I have to have earned that trust, that they’re willing to make themselves vulnerable and telling me more about this very uncomfortable thing.

Matt: So how do you build trust besides giving it? Or is that the only way?

Scott: The last therapist that I saw, she said that that’s the only way. [laughter] 

Matt: Oh! 

Scott: She told me and my wife, we were in marriage counseling, that that is the way. If you want to trust someone, the only way to do that is to give them something that you’re entirely sure you should trust them with. There’s no other way.

Matt: Hmm. That’s powerful and terrifying and everything all at the same time.

Scott: It is, it is. But if I have a dog and I need someone to watch it and you’re the only friend I have around — I’m not sure how good you are with dogs, I can’t half-have you watch the dog. Like, either you’re going to watch the dog or you’re not. Or either I’m going to let you cook a meal for me or not. Or I’m going to let you drive my car or not. There’s no — you can do things to insure and mitigate the dangers but either I am trusting you to do something or I am not.

Matt: I will say also that’s something I learned a lot when you joined because as one of the first middle managers, it was a lot of letting go for me.

Scott: Mhm.

Matt: The book is so interesting, especially looking back at it now, because it was a vignette in time and so much has changed since then. In fact, some things in the book quite embarrass me now. I was like, wow, I can’t believe we did that or like, we were so early in our journey in a lot of ways that the company in a ton of ways is unrecognizable in a way I think is really positive. 

You mentioned earlier that people still ask you about the book, you still get questions about it, so I guess people are still reading it, which is cool. How have those questions changed or what have you seen as the things that you look back and are like, “Oh, I’m glad that that’s better now,” or that we know more now?

Scott: I get asked a fair amount about the genderedness of my point of view. And it’s a regret.

Matt: I think it’s also a mistake I made when creating that team.

Scott: Well, maybe. That’s for you to —  [laughter] I know that — I thought about it in writing the book and I knew the culture of our team was a particular way because of its makeup. I should have put that in some kind of context and I didn’t. And part of that was — the book was supposed to be this insider view and I don’t do that much context-setting about these wider issues in not just tech culture but culture at large. I totally understand that perception and I’ve tried to explain it. I don’t think that was an accurate reflection of the whole company. I was trying to reflect what was going on in my team and I didn’t do enough to set that in some kind of context. I regret that.

But people ask me about the book because they’re switching to a remote company or they’re thinking about going to work for a remote company and they want to understand [what it’s] like. A lot of my answer is I don’t think remote work is that big a deal. I don’t understand why people obsess about it. I was at the gym today walking around the gym, I see people who are on their phones, people who are talking to their friends, they’re not necessarily doing remote work, they’re doing remote interaction with other people. 

Remote is such a part of our culture now. Anytime you’re on your phone, interacting with another person through a screen, and it could be an iPad or a laptop, you’re doing remote work. People do remote work at their non-remote jobs all the time and in some cases it’s 50 or 60 percent of their time at work. 

Matt: They’re not always talking to people presently, they’re often chatting or emailing with them.

Scott: Exactly, yeah.

Matt: They just happen to be in the same building.

Scott: Just email alone, ask people how much time of [their] day is spent on email. Guess what, that’s remote work. Remote work! But somehow there is this phobia and stigma around it that is really still strange to me. There’s this fear of it being this completely different way to work. Now it could be if you took a centralized team and one day just said everyone you’re going to go to different countries on the planet, that would be a radical difference because people’s lives would change. But in terms of how work gets done, we’re already remote workers. Everybody. 

If you do email, if you’re on the — you send text messages, Skype meetings, Zoom calls — to me it’s all remote work. And I try to tell people that and they still think there’s some other magical secret. And I’m like, no, I don’t think your problem with remote work is about the remoteness of it. Your problem with remote work is probably you don’t trust your team, your boss is a micromanager, you don’t have clear roles, you don’t have a good way to define who does what projects or to track them. And that’s got nothing to do with remoteness, that’s just basic competence as a team. 

Matt: I think part of it is it’s tied in with a bunch of other things. I like to say any organization over 25 or 50 is distributed already, they’re just maybe not conscious of it. But people, when they hear remote, they also think “Oh I’m working from home.” And their context of what they do at home is very different from what they do at work and sometimes it’s hard to bridge that. Like, how could I work at home with my cat bugging me all the time, or my kids knocking on the door and wanting to play? So that all gets bundled in with some of that. And some of those are real challenges.

Scott: Sure. Part of the stigma around this topic, it’s there is a totality to it that people feel that somehow they’re going to be forced to do things they don’t want to do. I have friends who commute to work and it takes them an hour and a half to go each way to work. I would never do that. There are so many different styles and formats and the demands on you as a person, what you have to wear as a dress code — No job is perfect for everybody. And so I’m an advocate for remote work, I think there are so many advantages to it, but I would never say that everyone is going to love working remotely all the time. I know this is true at Automattic, that some people join and after they’re there for six months — or any distributed company — they discover some things about their own needs they didn’t know before. They need more social interaction, they need more this or that.

Matt: Yeah. In-office work bundles a lot of things and for many people it also becomes, like you said, part of social — people you get lunch with everyday. It’s your connections outside of your normal circles. It’s maybe, depending on where you work, who you play volleyball with or who you exercise with or all these number of things. I think that’s actually one way that companies draw people in quite a bit. I frequently give the advice when someone joins to get some hobbies, go to some meetup groups, find some things where you can interact with other homo sapiens outside of this remote, computer-mediated interactions. 

Scott: Yeah.

Matt: The people who often have the most trouble with it are [the ones] where it’s their first job out of college.

Scott: Interesting.

Matt: You probably remember some of this. You wind up with this thing where someone is not being as productive after a little while and you’re like — I mean it’s a little silly but like, “Are you leaving the house?” [laughter] “Are you showering in the morning, are you eating things other than pizza?” You do need a level of discipline and an approach to healthy habits.

Scott: That is true.

Matt: Another key point and a prominent feature in the book and your experience at Automattic that you helped create was meetups. So we’re distributed, why do we need to get together?

Scott: That’s a bigger version of the voice comment that I said before about how our brains have old programming, we respond in certain ways regarding intimacy by being around people. Facial expression, body language, sharing a meal together.

Matt: Breaking bread, yeah.

Scott: Breaking bread, yeah, there’s a real power to that that you can’t quite replicate it, not in the same way. And so the meetup thing was something that you offered as a policy. It just so happened that me and my team decided to be the — [laughs]

Matt: To really take off on it.

Scott: To run with it. But I thought it made total sense to me, that at least a couple times a year, get everyone in a room together, and then we could flip the way we work and we could work more like a traditional team and take on a bigger project where we all have to be working on the same thing together for two days. 

There’s a different way you learn to work with each other when you have that kind of commitment. I think that helped us a lot as a team because then we’d go back to our regular style of working but now we just spent two days really working hard on something that stretched our relationship and our working styles in a very important way for us.

Matt: How was your trust before and after those meetups?

Scott: Probably better. This gets back to human psychology again. When you share a house with someone, you share a meal with someone, you trust someone to go get the groceries or pick up the car or do a dozen logistical things that happen to be required. It’s a little bit different than this person that you work with but it’s all through digital and virtual stuff. And I don’t know that a team needed to meet up as often as we did. We probably met three times a year and then there’d always be the grand meetups. That’d be the fourth, but we all really enjoyed it and we were all mostly — we didn’t have kids or families so it just fit our team style for the most part. That would change more as the team got bigger. 

Matt: I think this is probably an independent variable from being distributed or not but I’m a big believer in it, that if you give teams autonomy to try things out, hopefully the best practices then spread organically. And then occasionally you might come down from on high and say okay, everyone must do this. 

Actually the last time I remember that was with Slack because we had portions of the company on IRC and Slack and the network effects of having everyone on the same communication tool was too big, too important to let that be too balkanized. But the initial adoption of Slack was just on a team here or there. 

Scott: Yeah, that’s smart how you’ve managed that. I think the autonomy is really important to creative people and not in a superficial way. I think that their tools are so important. A big corporation that hires programmers and tells them you have to use this old computer or something, that’s a lack of respect for what you hired them to do. They’re going to be really tuned in to what tools are going to make them most efficient. Continuing to have that flexibility as Automattic has grown — that’s a cool thing. A lot of companies struggle with that as they grow.

Matt: One thing that comes up a lot is people not sure how to do — is like, “OK. my team is in five different countries, how do we brainstorm? How do we do that sort of creative frisson that seems much easier to spark when you’re in person and have that white board on the wall?”

Scott: For me, I didn’t struggle with that that much. I felt that if I have good people, and there’s a clear goal, then there will be an abundance of fodder. As long as stuff is being offered, as long as there’s that loop of feedback: idea, opinion, critique, new idea. You’re doing above the bar for most teams at most organizations.

Matt: Similar to one of your earlier answers that maybe it’s not as big a deal as people worry about.

Scott: I don’t think so.

Matt: So they should just try it. 

Scott: I think they should try it. But again the things I mentioned are not common. Talented people? Not common. People who are comfortable offering an idea and getting feedback on it? Not that common. People who are good at giving critique? Those kind of conversations? Most organizations don’t do that well. That’s really the problem to me. And no tool is going to solve that. It’s these other factors that are harder to deal with and probably have a lot to do with you as the boss. 

Matt: I’m a new manager at a distributed company. What should I do every day?

Scott: Lurk where your team communicates. Just lurk, just hang out. Spend an hour not jumping in. It’s very easy to jump in. Just observe. Because you may observe the team is just fine without you jumping in.

Matt: And then do you stack something on top of that later?

Scott: The thing that’s coming to mind is whatever feedback loop you have with each individual person on your team — and there is a set of questions that I developed. It’s in the book. I think the four questions were: what’s going well, what could be going better, what do you want me to do more of, and what do you want me to do less of as a manager? That’s how very one-on-one conversation I’d have — which would be like a half an hour, whatever, once a month or so — would be framed in those four questions. 

Matt: Twenty years from now what percentage of jobs do you think will be distributed?

Scott: Well, so I spent a fair amount of time, not recently, with some of these statistics because I get asked a lot and it’s weird how they measure these things. This will be my way that I dodge the question is to talk about survey design instead.

Matt: Telecommute.

Scott: A lot of the surveys are designed, they ask the question in the sense of you being a hundred percent remote or days where you’re a hundred percent remote. So it’s really weird because there are some companies that have liberal policies for you taking one day a week to telecommute. Is that remote work? Well it is but how does that fit into a percentage, like what you’re asking? It’s a weird thing.

Matt: We can make our own definition here. If you were to pick an integer that was a percentage and let’s say people who work not in an office the vast majority of the time, the plurality of the time…

Scott: Yeah I think all the numbers will go up, to cut to the chase. I think it has to. The tools — I’ve already made the joke that most people are already doing remote work even though they don’t call it that. That’s just continued to grow. The tools will get better and better and all the things that can be done digitally, which is the cliff to get over, the curve to get over before you can do it on your phone or your tablet, will continue to grow as technology gets better.

Matt: So a hundred percent? Wow. 

Scott: Well it can’t be a hundred percent because you don’t want your brain surgeon working remotely or your —  

Matt: There was famously the doctor that wheeled in on one of these iPads-on-a-wheel thing and delivered a terminal diagnosis and the person was upset.

Scott: Yeah. I see. Yeah that’s a tricky one. That’s a whole other case though where —  

Matt: It’s a good chance to switch mediums.

Scott: Yes, that is a good chance to switch mediums. Someone else should’ve given the diagnosis I think. Yeah. But I’m very positive just because I think that more worker autonomy just makes for better work. I really believe that.

Matt: Just pick a number off the top of your head.

Scott: What do you think, this is five percent now? Of jobs that are distributed?

Matt: Sure.

Scott: I don’t know, ten percent? I don’t know, twice that, maybe three times that. 

Matt: So somewhere like 25 to 35 percent?

Scott: Yeah. I think it’d be. And that’s enough for it to be normal.

Matt: All right, we’ll get you on Episode 15,000 of the podcast and we can check it out.

Scott: [laughs] Reserve my slot for that.

Matt: Where can people find you if they want to hear more?

Scott: I am ScottBerkun.com and I’m @Berkun on Twitter.

Matt: Scott, it’s always inspiring. Thank you so much for talking with me.

Scott: Thanks for having me.

Matt: That was Scott Berkun. His latest book is The Dance of the Possible: The Mostly Honest Completely Irreverent Guide to Creativity. You can find him at scottberkun.com. 

Thank you so much for joining us and see you next time.

Read more about Cate Huston in “How to Build and Strengthen Distributed Engineering Teams.”

Cate Huston is the Head of Developer Experience at Automattic, where her team is responsible for hiring, onboarding, and retaining some of the best software engineers in the world. In this episode, Cate talks with Matt about what kinds of people thrive on distributed engineering teams, and how team leads can keep their engineers happy, productive, and connected to their colleagues. 

The full episode transcript is below.

***

MATT MULLENWEG: There are all sorts of approaches to distributed work. Some people work from home or at a café in their neighborhood. Others are digital nomads. I’m Matt Mullenweg, the CEO of Automattic and co-founder of WordPress, and I travel around 300 days out of the year. I appreciate that I get to spend time with my family in Texas, but I love life on the road too, and being able to hang out with friends and colleagues all over the world, and meet WordPress users wherever they might be. One of the nice things about running a fully-distributed company is that even the CEO gets to be just as remote as everyone else. 

Today’s guest is Cate Huston, who is a true digital nomad. All she needs is a cup of tea and a place to set up her laptop and she’s ready to go. Her home base is the city of Cork, in Ireland, but you’re just as likely to find her in any other corner of the globe.

Just because Cate is always moving doesn’t mean she has trouble staying connected. Her role at Automattic requires her to be in close contact with her team, and it’s her job to help make sure that all of her fellow engineers stay connected, too. 

After leading several engineering teams at places like Google and others, Cate became the Head of Developer Experience at Automattic, a team responsible for helping all our engineers at Automattic stay engaged, productive, and professionally fulfilled. 

I knew we had to talk to Cate on this podcast because she lives out the distributed model so fully. She also has a comprehensive point of view on what kinds of engineers excel in distributed environments, and how companies can create the conditions that help engineers thrive.

Alrighty, let’s get started with Cate. 

MATT: Hello Cate, thanks for joining today.

CATE HUSTON: Hi Matt. I’m ready for a one-on-one.

MATT: [laughs] Ahh I forgot to tell you we’re recording it. 

CATE: [laughs] You should warn people about these things.

MATT: For the audience, can you catch us up a little bit on some of your experience that led you to Automattic?

CATE: I worked at Google as a software developer and then spent a year roaming the world and doing my own thing, and then joined a startup and was a questionably-legal migrant in Colombia for a while, and then that startup kind of imploded. And around that time, you sent me a GIF of a raccoon being adorable and I was like, “Okay, he can be my new boss.”

MATT: [laughs] You joined to lead the Mobile Team at Automattic.

CATE: Yeah.

MATT: But that has grown. So talk a little bit about that. 

CATE: I joined towards the end of 2017 to lead the Mobile team, which was amazing. And then after about 18 months I went on rotation to the Jetpack Engineering team, which was also super interesting because, as you know, I’ve been using Jetpack for a long time too. But when that came to an end it was clear that I was more needed elsewhere. So I didn’t back to the Mobile team, and I got to work with you, and rolling out Gutenberg. And now I lead our Developer Experience team. So we work to support our entire developer organization, and that includes owning the engineering-hiring process. 

MATT: What is developer experience at Automattic? I’ve heard of user experience but what does developer experience mean?

CATE: I mean: “What does it mean to be a developer at Automattic, what are the challenges of development at Automattic, what are the challenges of development in a distributed, remote context, how can developers learn from other developers, how can they have the support that they need to chart out their own career path?”

We have a lot of autonomy at Automattic, which I think is amazing, but that autonomy can be a bit overwhelming. So can we turn it for people [from] “Write your own MadLib,” into “Choose your own adventure,” [giving] people that kind of support. Also a critical part of the developer experience is the hiring experience going through into the onboarding experience. So how do we give people in our hiring process a good experience so that they can see if this is the right fit for them and we can see if they are the right fit for us, and how do we carry that through into them joining their team and becoming successful?

So one of the ways that we think about developer experience is — our engineering organization is quite big and we’re only so many people. So what we talk about is, “How do we find the pivot points for individuals in teams so that we can be present at those pivot points and try and make them accelerants where possible?” An example of that is when the team gets a new lead, that’s a pivot point. So we want to be there supporting that new lead, bringing them into the kind of support that we have for dev leads, helping them develop and iterate on their process so that that new lead can take that team to new levels. 

MATT: There are probably some engineers listening right now who would love to be hired at Automattic or another distributed company. What advice would you give to them?

CATE: The first thing I would say is, “Be patient, because I think all distributed hiring processes take a little longer.” I think people feel — I don’t know if it’s true — that they get a stronger signal in a day of face-to-face interviews but I think people feel like they have a stronger signal in a day of face-to-face interviews. 

And distributed companies, you can’t tell really if someone doesn’t show up to work. I mean, you can eventually tell, but it’s much easier to disappear. The level of trust required is much higher. And so there is a portion of the process that is earning that trust. We really believe that people can be successful and we’re looking to make people successful. There is no “prove it again” after you get hired. I think that’s really important.

So the first thing is patience and just understanding that the processes take longer. The other thing is that these jobs tend to be more competitive, especially for more specialist roles. There’s not always as many of them as you might want. So you want to craft what you’re doing a little better. Tell a good story in your cover letter, get excited about that company specifically, not just remote work in general. I’m sure all remote companies get a lot of the kind of applications that we get, which is like “Yeah, I just want a remote job so that I can travel around the world.” And it’s like, “Okay, it’s cool to travel around the world, I do it, you do it, but it’s not easy to do that on top of a full time job.”

MATT: So what’s the key for maintaining high performance, as you do, in all these far-flung locations?

CATE: I get pretty rigid about certain things. Like breakfast, I’m very rigid about. So every morning there’s breakfast and then I – 

MATT: That’s very British.

CATE: [laughs] Very British. British being rigid or breakfast being important?

MATT: I think breakfast.

CATE: [laughs] So I try and carve my day into two four-hour blocks. And I just don’t expect to do anything fun during the week, so I do my tourist-ing on the weekends. I really just go and spend a month in a place and try to live there. And honestly I live like that most of the time. When I’m in Cork, because I live in Cork, I try to do things on the weekend, get away from the computer, go out and see things. So if I’m doing that in a different place, it’s fine.

I have my certain needs, which are pretty minimal, like breakfast and some form of exercise and that’s it. And so I just orient myself on “This is breakfast and here is a place to work, there is tea, and this is how I’m going to get regular exercise,” and then, honestly, that’s fine, that’s all I need. 

I’ve probably paired down these needs over time. I don’t know if I started that way, and it is quite hard if you need more stuff. I think sometimes people want peace and quiet, for example, or they need more social contact or whatever, and things that take more time to build, but for me, a laptop, a pair of headphones, a good amount of tea, everything’s fine.

MATT: When you’re hiring engineers, what are you looking for as part of this process besides obviously some base technical-level skill?

CATE: Probably two really big things. One is the ability to work with the kind of code base that we have. WordPress has been around for a long time, there’s probably still code you wrote floating around in it, and that’s quite hard. Not everybody has the experience, the desire to work with truly legacy code. 

And it is a very complex system. It’s not just about technical capability but it’s also being able to grok the complexity of what we had. And this is something that we saw in the mobile apps as well. We would have people on trial for that. There would be three networking stacks because the mobile apps have to speak to WordPress.com, they have to speak to Jetpack, and they have to speak to every other WordPress site too via XML-RPC. 

There’s just a huge amount of complexity that comes with that. And if somebody has not worked on something that is really complex before then they’re going to have quite a bad time with that. And we want to see how they can adapt to that complexity, how they can work with it, and how they can deliver things. 

The second thing that we pay a lot of attention to is how well do people respond to feedback. We are not really hiring people just for what they’re capable of today, but we see it as a long-term commitment. These people, we want them to stay with us for a long time, right? So we’re also hiring them for their growth and the growth that we believe that they can do. And the best predictor of that is that they respond well to feedback. So if we give people feedback and they take it and multiply it and do a lot better, then we feel way more excited about hiring those people than the people who take the feedback and they’re okay with it. And then of course the people who don’t take the feedback well at all, we reject them.

MATT: How have you grown in learning how to take feedback well?

CATE: The first thing is working on self-awareness. When people are not self-aware, you can’t really connect with them because you are always being indirected by their ego. And so developing your self-awareness is super important, something that I work a lot on.

MATT: What does it mean to be self-aware and how do you develop that?

CATE: Do you tell stories about yourself? Do you have things about yourself that you really need to believe are true but might not be?

MATT: What’s an example?

CATE: Some people want to be seen as really nice or really caring, for example, but they might not be very caring. And so they’ll talk a lot about how caring they are but they’re actually not. And so this gap between the way that somebody talks about themselves and their actions will show you this gap in self-awareness.

MATT: How do you cultivate self-awareness?

CATE: Just disabuse yourself of all your illusions. 

MATT: You make it sound easy.

CATE: No, it’s horrible, it’s a lot of therapy and coaching and just being willing to confront the pieces of yourself where you know you’re not as good as you would like to be. Second thing, broadening your perspective, being more open to possibilities outside your worldview. So reading fiction is demonstrated to make people more empathetic, but then reading a broader variety of fiction written by people who are not like you can also broaden your self-awareness. Cultivating a broader network of people, making sure that you’re connected to diverse voices and people who are not like you. And then traveling outside your comfort zone. We talk about the digital bubbles we live in, but a lot of us also live in physical bubbles. And for me, I spent a lot of time living in Medellin, and existing in my third language was a profound exercise in human limitation and empathy.

MATT: Totally. I’d also say you can travel outside your comfort zone without leaving your city.

CATE: One hundred percent.

MATT: There’s probably parts of your city or places that you haven’t been to, buildings you haven’t gone into, places of worship, neighborhoods, stores, barbershops, that can be a journey as well.

CATE: Totally. I am right now in a part of Cork that I had never been to before today. I did not know it was here. So shedding defensiveness, you know? I think people’s first reaction to feedback is to be defensive. It creates conflict, it means you don’t really learn what’s happening, and it shuts the conversation down or it makes the conversation about your feelings rather than what this person is trying to tell you.

Something my coach always tells me is “get curious.” So learning to be — if something makes you uncomfortable not to shut down but to lean into it and to ask questions and really try and understand it is super helpful. Something that people do here is offer context. So people give you feedback and what you give them back is context. And to a certain extent that’s fair enough but too much context is just a polite way to defend yourself. 

MATT: Someone says, “You need to improve X, Y, and Z.” And you say, “Well this and that and this was going on.” Is that what you mean by context?

CATE: Yes, or maybe like, “Oh, you know, I didn’t like how you responded to X.” And then it’s like, “Okay, but for context this set of things was happening.” It’s not really helpful. It’s also getting ahead of that, right? If you say, “Cate, you’re missing your goals.” And I say, “Now let me give all the reasons why this is hard,” that’s not a healthy conversation between us. Right? 

So I’m always trying to get ahead of that with you and be like, “Okay this is where we’re at, this is what’s going on, this is what I’m worried about, this is what I need your help with,” so that you know that you’re not finding problems and giving to me because I know my own problems, and I am on top of them, and I’m telling you what’s going on and what I need from you, so that you should know that you can trust me.

MATT: Got it.

CATE: Asking for advice is also very helpful in self-awareness. Often people are afraid to give feedback because they don’t want to upset you and they are particularly unwilling to give you feedback if they think you’re doing a good job. It’s like, “No, no, no you’re good, you’re good.” But they might have some advice for you.

MATT: So just changing the word you’re using can change how people respond?

CATE: Totally. We have all these negative connotations about feedback, but feedback is really just your own being-in-the-world and being-at-work, for example, being reflected back to you. And it’s neutral really, or it should be. When I’m writing feedback for somebody, the question that I will ask them when I give it to them is, “Did you feel seen when you read this, did you feel like I see everything that you’re doing that’s great and everything that you’re capable of, and how you can do better?”

MATT: Something I try to remind myself, especially when I’m receiving feedback that might be tough, is that good feedback, and by good I mean it’s thoughtful, is a gift — feedback is a gift. And when you receive that you can use it well or you can use it poorly. And I love what you said around getting curious. That is a nice way to reframe something that might be challenging. 

CATE: Yes. If somebody cares about you enough to tell you that they think you should do better then it means that they believe that you could do better.

MATT: What else is on the list?

CATE: There’s two more. The other one is stop giving advice. [laughter]

MATT: That seems incompatible with receiving advice.

CATE: Most people are way too willing to just give advice without context and often without even understanding what someone is trying to achieve. Declaring a moratorium on advice can at least make us pause and ask questions and get context and reflect back to someone what they’re saying to you. 

And the last one is to own up. If you can admit what’s not going well then it’s much less scary for people to talk about the details of how that didn’t go well or what’s not going well. So again you can just make it easier for people to give you information that you wouldn’t otherwise get. 

So my team doubled in size recently. I put up a post on our P2 and I was like, “Okay, so our team has doubled in size and clearly my job is going to change too, and these are the ways where I currently see myself not doing as well, and what do you think? What do you need from me?” And I asked these structured questions to get feedback around what’s the most useful thing that I do for you or what do you think I should stop doing. 

And I got all this amazing input from my team. And if I hadn’t just straight-up admitted it in public, maybe they would be in private being like, “Ohh, Cate seems really frazzled, I don’t know what I can expect from her, I guess I understand that the team is bigger now…” But they might be afraid to tell me what they were experiencing. Whereas instead, putting it out there and having that conversation together made it a team change and a — My job is just the piece of how our team works and we are all deciding and designing that together.

MATT: I know you’re passionate about engineering management. One area where engineers do this a lot is in code review.

CATE: Right.

MATT: Pull requests, etcetera. So what do you see there and what are you working on or want Automattic to work on there?

CATE: I think code review is a core function of a healthy engineering team. Code review done well is such a powerful collaboration tool because both people, or anybody involved in the code review, is learning what the person who wrote the code did, the questions the other person asked, and the reviewer asked. It’s a structured way to have a conversation about the task itself and also the long-term [project] of the code base.

MATT: What else makes a great engineering culture?

CATE: Something that we used to talk about on the mobile team was that a senior engineer makes the whole team better, but we don’t want to be prescriptive about how people made the team better. That was up to them. There were options, but that was the expectation for everyone on the team. It’s like, you come in, you’re an experienced engineer, we expect you to be making the whole team better in some way, and what that looks like is up to you. 

That captures my aspiration for a great engineering culture because one, it suggests that everybody is additive and two, it suggests that everybody is allowed to be unique. And three, it suggests that everybody has the autonomy and the support to operate from a place of strength.

MATT: How much of this is specific to being distributed? How much of this was true when you were at Google versus what might be different now in a distributed company like Automattic?

CATE: The thing I think about distributed is that it makes the things that are hard explicitly hard. I don’t think it really changes anything.

MATT: Tell me more about that.

CATE: You might say that getting a team to be coherent and inclusive and what have you, is just intrinsically hard. And if you are collocated, then you might say, “Oh no, my team is very coherent, we have lunch together everyday, and we do stand-up together every morning, and every so often we do some group activity together. Our team is very good.” 

Whereas if you’re distributed you’ll be much more intentional about it. You’ll say, “Okay, well now I have a new team, and I want that team to be coherent, so how do I make it coherent? How do I make sure that the team understands what their mandate is? How do I make sure they understand what their priorities are? So how do we really maximize the value of a meetup so that people come away the most aligned that they can be?”

MATT: I think it’s helpful for us to be very real on this and talk about the downsides of distributed as well as some of the upsides, which we cover pretty extensively. So to be real and candid about Automattic, what do you think are our biggest challenges and weak points right now?

CATE: I think that we have not always done a great job of hiring and onboarding senior leadership especially into the distributed context. Sometimes we hire people who see distributed as a thing that needs to be mitigated or worked around, rather than a thing that you work with. I don’t think we’re delivering particularly well right now. I don’t think we’re shipping enough and I don’t think we’re shipping enough user value. 

MATT: Totally.

CATE: And I think we’ve evolved our org chart in ways that have been more disruptive than we realize, and have created a lot of gaps that it’s not clear how we should fill or if we’re going to fill. The way that I think about org charts is that they’re really just our chosen optimization, and we can choose what it is, but we have to manage it. 

And I think the thing about a distributed context is that sometimes you can choose your new optimization but if you don’t do the change management it’s not always as obvious what’s going on. Like if you’re in an office and morale is low, you feel it. But in a distributed context it feels different.

MATT: Cate, those are definitely some good challenges. One that has been on my mind recently is I’ve noticed a lot of negativity in some of the teams and some of the feedback. What are your thoughts on that and where does it come from? What can you do to address it?

CATE: I think people get increasingly negative when they don’t feel heard and when they don’t feel hopeful. And so I have spent a lot of time listening to people be negative, and have them not see the value of things that I’m doing. Hearing them out has always been really important and some people will never come around, and some people just need to feel like they’re heard, and to get some of the context that they may be missing, and to have a reason to hope.

In one of my Quartz articles I wrote about how, in any kind of period of change, the people who struggle most are the low performers and the high performers. And the low performers struggle for very obvious reasons, like, change is difficult for them because it’s potentially threatening. They know they’re not amazing. And so for those people, often you can make change good for them, because hopefully you can help them level up. I don’t believe anybody thinks, “Oh I want to be mediocre at work today.”

But then for the high performers, the things that they struggle with, is that they have found a way to succeed in the system as it is, and so any change seems unnecessary to them because really, the problem is that other people haven’t figured it out the way they have. And so those are people where — they’re to some extent right and to some extent wrong. And so helping them have the context, see the empathy, experience the empathy and see some reason for the change and helping them see a sense of improvement is really, really important, because you need to bring those people with you. 

If your high performers are not bought into what you’re doing, then other people won’t be bought into what you’re doing either. So you spend a lot of time, or I personally have spent a lot of time on the high performers who are like, ‘Yeah but really other people just need to be better.” It’s like, “Well, yeah, they do, and so we’re going to help them be better now by doing these things,” and eventually they’ve seen the value of it. And that has generally brought me a disproportionate amount of credibility with other people on the team. 

MATT: Who might distributed work be excluding that might be more included in an office environment?

CATE: Extroverts. Offices give people a certain amount of structure and community, and in the absence of that you have to create your own, and not everybody can or wants to. Work is really just one part of life. When you talk about distributed work, that’s great, there’s all these things that we can do. But when I onboard people into a distributed context, especially for developers, they don’t tend to struggle with the work aspect of it. 

But what they do struggle with is the life aspect, especially people who have not worked in a distributed context before, or a remote context. They struggle to give themselves the structure in their day. They can start work whenever and so they do, and then they finish work at 2:00 in the morning. And at some point, some people are genuinely nocturnal and — fair play, but most people are not actually nocturnal. And starting your day at 4:00 in the afternoon and working until 2:00 in the morning is maybe not that good for you. It’s normally quite bad for your social life unless you are friends mainly with bats. 

So there’s a bunch of knock-on effects to that, which affects your social life, it affects their life-life, it affects their health, because they’re not getting enough sunlight, exercise, what have you. So as someone’s manager, I care about them as a human being, but I’m not their mom. And so that can be quite hard because often it affects their personal well-being more than it affects their work, but it will ultimately affect their work too.

MATT: How can managers encourage inclusion, especially when they might have people across normal categories that we talk about, but also across countries and everything?

CATE: You have to be explicit and talk about it and measure it. In all our reporting on hiring, you will find the same words, which is “Diversity is more than gender, and gender is not binary.” But this is what we can measure and so we measure it, but then we do almost nothing that is just targeted at women. We just use it as a metric and as an indicator of diversity. And we talk about it very explicitly, constantly. 

And I think being explicit like that is really, really helpful. I think being very vocal that it matters — in tech now, I feel like we have talked about diversity maybe too much, inclusion — not enough. And now if you’re not saying, “Oh inclusion is very important,” then you’re clearly a terrible person. So we’re all saying inclusion is really important, but what are we doing?

And then the final thing is building that human connection and checking in with people. I think there are a lot of things that we miss when we don’t see people in person, and you have to notice when people are quiet. And that actually is something that requires a lot more attention.

MATT: Cate Huston, thank you so much for sharing both the good and the bad about distributed work. I think there’s a lot of wisdom in the things we’ve covered.

CATE: Thank you, Matt. I appreciate you.

MATT: That was Cate Huston. You can follow her on Twitter at @ C-A-T-E-H-S-T-N.

I mentioned earlier that there are different approaches to distributed work. And that’s not just true for travel habits. People with different personality types prefer different levels of socialization, communication styles, and leadership styles. Some managers love to have lots of meetings and others would rather keep things moving in the Slack channel. This diversity of styles can make Cate’s job challenging, and as a leader of distributed teams, it can make mine pretty challenging too. 

But I also think this is one of the things that makes the distributed model so exciting. It’s easier for us to meet people where they’re at and give them a custom work experience that suits their personal style. This ideally makes for happier employees and better work. 

Next time on the Distributed podcast, we’ll be talking to author Scott Berkun, who once worked at Automattic and wrote a book about the experience called The Year Without Pants. I’m going to talk to him about his time as our first Team Lead, and about how the distributed-work landscape has changed in the last seven years. 

Thanks so much for joining us and see you next time. 

Read more about Leo Widrich in “How to Stay Connected in a Distributed World.”

Leo Widrich co-founded Buffer, the social media management software company, in 2010. But like many founders, the frantic pace and daily stresses of startup life caught up to him. After spending a couple of years in a Buddhist monastery studying mindfulness and learning to build emotional resilience, Leo now coaches other business leaders. In this episode, Leo shares tips for distributed workers on how to build healthy habits and avoid the “loneliness spiral.” 

The full episode transcript is below.

***

Matt Mullenweg: Imagine starting a company with your buddy, turning it into a multibillion dollar business, and offering a service used by brands all over the world, and then walking away from it all to live in a monastery. That’s exactly what this week’s guest did. We’re going to hear all about why he did it. With the startup Buffer, Leo Widrich has achieved success by any measure. But something was missing. His dissatisfaction with the lifestyle led him to pursue deeper truths that he came to realize cannot be found in the pursuit of material success.

Leo studied Buddhism. He spent some time living with monks, and learned to appreciate an intentionally slow lifestyle. Now, he coaches entrepreneurs and even other coaches with the goal of helping them manage the stresses of their careers with a combination of ancient wisdom and a sprinkling of modern neuroscience. He wants people to learn how to build emotional resilience, and the ability to self-regulate their emotions so they can deal with their issues and avoid the full-scale burnout that he suffered.

Buffer is a remote company, so it’s clear that Leo has a passion for unconventional work arrangements. However, he’s extremely sensitive to potential emotional and psychological pitfalls associated with working from home. In this episode, I learn about the loneliness spiral, what can happen if you don’t exercise your social engagement circuits through regular social contact, and Leo shares a few tools that we can use to care better for ourselves and the people we work with.

Leo Widrich: I started a company called Buffer close to a decade ago with a friend and we worked completely remotely.

Matt: Where were you both when it started?

Leo: We both first lived in Birmingham, U.K., so in England, we both studied there. And then we flew out to San Francisco and said hey, Silicon Valley is the spot. That’s how we got started. And we went through all the startup struggles and ups and downs and a couple of the things that were really wonderful as we built the social media management software. And we did it eventually fully remote also, to a level of transparency where I really wanted to put everything on the table about what was going well and what wasn’t going so well in the business. 

Matt: An unheard of level of transparency. So Buffer publishes its revenues, its salaries, its options. Everything, right?

Leo: Right. That was a real desire for us to bring that level of transparency to the business world to reduce some of the sense of secrecy and some of the sense that this is a fight and make it a little more collaborative. 

Matt: Tell me about the why there. Why were you distributed if you started in the same place? And then why the transparency? And are they related at all?

Leo: I think that the distributed part — we were in San Francisco and the team was growing and I’m sure you know that as the team grows in San Francisco, your office space needs to grow. And we were in the middle of — should we expand and get a new office? And I remember even meeting with some brokers, and the prices, they seemed incredible. And we were like, huh… And some of us were barely even coming to the office. 

And I think that was a moment where we all thought, “Well why don’t we try not being in the same office.” And we had tried that before because of visa problems. So at first that was totally not a choice, we just had to be all over the world because we couldn’t stay in the U.S. My partner, Joel, he was from England, and we had a third cofounder, he was also from England. I was from Austria. So it was really hard for us to actually be in the country, so we had to be distributed.

But eventually it was a question of cost and a question of joy and ease too, right? Like, “Oh, why don’t we get to work from wherever we want to?”

Matt: Great. And when was this?

Leo: It must have been 2013, over six years ago, that we decided — before it was unclear, more like an unwritten rule, because we were so small. But then we decided, no, I think we will allow people to be wherever they want to be and then make that a more official commitment, so to speak. And that was also the time when we did start to be more transparent because we wrote down our values, we were very inspired by a company called Zappos at the time.

Matt: Yeah, of course.

Leo: Right? Tony Hsieh is a real mentor in that space of really defining your values and having your purpose. And that was also one of the things that came out of that. So committing to working remotely and committing to being transparent as a way to share with the world what we are learning and to foster a sense of collaboration and openness.

Matt: What was your biggest lesson from being distributed like that?

Leo: At first it was so wonderful. We were traveling around the world, we got to really live a life as well as we were working. So we weren’t deferring enjoying life, so to speak. But over time for me personally what started to creep in a little more was this sense of loneliness, this sense that I feel not as connected. I don’t need to have a base so I’m not committing to a base, that untethered-ness, the longer it went on, the less enjoyable it became, the more almost-painful it became, I would say.

Matt: When you left Buffer, what was next for you?

Leo: I started to feel like I was hitting a wall. This thing that I always dreamt of, to have a profitable company, to be financially secure, to have a team, like a lot of things that I started to aspire to when I got in touch with this idea of startups early on — I felt that having that success, having some of that financial security — it left me unfulfilled in a lot of other areas. In the sense of deep lasting connection and also just a lack of emotional resilience to deal with the ups and downs that startup life comes with. 

So I felt exhausted and we weren’t quite fully in agreement anymore with my cofounder. And I took that as a sign and said “Maybe this is just no longer the right thing for me.” And I took my hat and I left and it started this really interesting journey from outwardly doing stuff and accomplishing stuff — which was the only thing I knew at the time — to go inward. And I started to go and live in Buddhist monasteries and do some therapy training and really start to understand — “Okay, there is so much I was externally striving for but what’s actually here? What’s this foundation, this house that is my body and my psyche?”

Matt: Wow, that’s a big step. Tell us about this Buddhist monastery.

Leo: It’s a big step and a lot of people at the time, they looked at me and they said, “Oh, you’re crazy.”

Matt: I’m so curious, is there an Uber for monasteries? How do you find where you go? Where did you end up? Just walk me through the whole thing if you don’t mind.

Leo: [laughs] Right, for sure. I started to become very interested and soothed by the writing of a Buddhist monk called Thích Nhất Hạnh, and that is really the person that I think brought me into this world. And he wrote this book called Peace Is Every Step. That was the first book I read. It really touched me. It set something off in me. 

He talked about a sense of living in the world and being in the world without that constant striving. And here I was finding myself striving so much, trying so hard to make something successful, to be successful, and he was challenging that idea. And so I saw him speak in 2013. That was when that was more on the sidelines. I was just learning about this stuff. 

And I was living in New York and there is a monastery called Blue Cliff Monastery in upstate New York that I wanted to check out. And I went there for a few retreats, to see what is this life like that seems the exact opposite from the rapid fire startup life, where these Buddhist monks and nuns were living, going so slowly, barely any agenda on the day, every day. And so it was this very different life, very slow. There was very little content, other than what was bubbling up from within me, right? So it was really making a lot of space.

Matt: So you went from startup founder to — I don’t know if you’d call it a monk but you were at a monastery for several years.

Leo: Right.

Matt: And now you’re like a coach. So you work with clients.

Leo: Yup. I call it emotional resilience training, that’s the tagline I have.

Matt: So assuming that you can’t tell your clients to also go away for two years…

Leo: [laughs] Right.

Matt: What’s a middle ground?

Leo: Yeah, you don’t need to go off for two years. But there needs to be some sense of regularity to coming inward, to coming internal. And that is what allows us to build that muscle of emotional resilience where we can not be so cut off from ourselves in the face of difficulty that happens to us and instead to flow with it, to surf the wave of pain, of anger, of sadness, whatever it is. 

And I started to incorporate that with executive coaching, with a framework that — yeah, and you want to also keep contributing to the world. A lot of people don’t want to just step away. Often times, they can’t, right? They have a family to support, they need to keep working or to have a startup to run. And so it became and it is still becoming this combination of offering this deeper emotional work alongside more dialed-in direction-setting for where you want to take your company or your career or your life.

Matt: Give me an example. You say you need this daily habit. What would be something I could do to start to connect and avoid that burnout?

Leo: If it’s possible to you, I would recommend to find something that is not solitary.

Matt: So not self-meditation?

Leo: Yeah, not self-meditation. I would recommend against that unless that’s the only thing available to you. I would recommend that, if you can, to find a therapist or find a coach or find a mentor in your company that you can have regular conversations. Or even a trusted friend — there is a beautiful practice that people can google, it’s called Empathy Buddy Calls. And if there’s a framework for this — how to have these deeper conversations with a friend because often they — even though we might trust someone or have a great friendship they don’t always go to these deeper levels and it’s a great framework. 

That would be my suggestion, to have some support. And the reason I think this is important is because the very idea to do things alone, especially for the likes of me, are only further perpetuating the way I see the world, that I need to be hyper-independent, that I need to pull myself [up] by my own bootstraps, that it’s about strength and doing things alone. And I find that again, back to an evolutionary science, is not really how we evolved, it’s not how our brains are wired, and it’s not as effective as doing it with another person.

Even when I lived at the monastery, it was so interesting that none of these monks meditate alone. Every meditation is together. And this monk, Thich Nhat Hanh, he emphasizes sangha so much. He says if you don’t have a sangha, which is a Buddhist word for “community,” it’s almost impossible to really go to the depth that you need to go to, to deeply transform within yourself.

Matt: That’s so interesting because I’ve definitely read also — I want to say it was Naval Ravikant who sort of made fun of how Westerners turn solitary things like yoga, meditation, into group activities and team sports.

Leo: Interesting, interesting. Yeah.

Matt: And I forget the exact tweet but I took it to heart a little bit because I do often like to exercise or meditate with at least one friend, if not more, and I was like, “Oh am I doing it wrong?” Maybe I need to be more comfortable being alone. 

Leo: Right. And I can see the point of that too. I can see the point of that. 

Matt: But your advice is different for your clients.

Leo: Absolutely. It has become different. If you had asked me four years ago, I’d been meditating on my own for years and years before going to the monastery. And I agree on the point that if it becomes a sport or if it becomes a co-exercise — that is not what I’m talking about. What I’m talking about is to enter spaces together that have a certain depth where you and I say, “If we were to do this together, I might still have a solitary experience, by you holding space for my experience.”

But from a nervous system perspective, the charge that is needed to allow some of these deeper things to come up through the vagus nerve and through my amygdala — in order for that to be held — the amygdala is the fear center in our brains. For that to be not going all over the place, having a second nervous system there to create a sense of safety, I believe is so extremely vital. 

Matt: So that would be your advice to someone starting out, say, find a buddy and do some of this more mindful activity together?

Leo: Absolutely. If that’s possible then I think it’s — and talk about it. 

Matt: We’ve used the word burnout already. What does that mean to you?

Leo: In the same way that the word stress — I like to use it less so. Because it doesn’t really give us a sense of what underlying thing that is happening. I think I even like to use the word PTSD better. 

Matt: That’s a heavy one.

Leo: Right, for most people that would sound heavy but most of — 

Matt: And it has stress in it.

Leo: And it has stress in it, right. But the interesting thing, when we talk about PTSD, and I don’t talk about the way it’s defined for psychologists, I talk about posttraumatic stress. And maybe we can leave off the “D” of disorder because I don’t really think it’s a disorder. But I think it’s anything that when we feel tense in our bodies, it’s because it’s posttraumatic stress. There has been a certain event in our lives and there may have been in our childhood or there may have been, you know, in a meeting or a presentation, and our brains weren’t able to integrate fully what was going on. 

So I’ll give you a common example. Maybe you’re a founder. You have a meeting with your board, and there is a very heated debate. You’re not getting the buy-in, you’re not getting the agreement for something that you really wished you could do. And you leave this meeting feeling quite distraught, feeling quite activated. Your nervous system is charged, you feel angry or you feel sad or there is something — you’re no longer regulated.

Now most people don’t have a way to resolve that. They have a way to auto-regulate and it’s different from self-regulation. And I’m bringing in a few terms here. But most people then auto-regulate. They have a glass of wine or they have a drink or maybe they watch something on TV to soothe themselves.

Matt: What does auto-regulate mean?

Leo: The way it’s defined in neuroscience terms is our natural, unconscious coping mechanisms to deal with deregulated states. And deregulated states means when we are not relaxed, in a relaxed alertness. So that means eating sweets, right? That’s a common auto-regulation pattern that I have. When things get tough, my mind sometimes goes to the ice cream tub in the freezer. 

Matt: For me it’s a matcha latte. 

Leo: Right, right. [laughs] 

Matt: If I’m tired from the day before I just like — you know, the afternoon comes along and I’m like mmm, matcha latte.

Leo: Right.

Matt: I deserve this.

Leo: Right.

Matt: And I get addicted a little bit to that. I don’t have very much caffeine usually. So it does have a big effect on me.

Leo: Right. And that’s a wonderful example. Auto-regulation doesn’t mean it’s bad. We all have that. It can have extremes, like heroin is auto-regulation in the same way that going for a walk in the forest is auto-regulation, right? It’s things that we don’t think about too much that just come to us that have been ingrained patterns and habits and we do them.

Matt: Is burnout avoidable?

Leo: I think so, when we have self-regulation. So self-regulation is a way to deal with the actual effects of what happened in the meeting and to fully process it, for example, if you go back to the example of the board meeting. The body always keeps the score of whatever we haven’t fully processed. 

And so the more of these episodes you have, and in a startup very quickly you might have a lot of meetings where things don’t go well and if you don’t have the time to self-regulate, to talk through this with a friend or with a therapist or with a coach or somebody or with a partner — some people have very healthy self-regulation coping strategies there, you’re actually getting to the root. 

After the meeting, say I had a hard meeting and you’re my good friend Matt, and we sit down and you ask me, “Hey Leo, how are you doing? You look a little upset, you look a little tired.” And I get to say, “Yeah, I’m so upset, this just sucked, this meeting.” And you reflect that back to me, you help me, and say, “Yeah it just sounds like you weren’t heard and you didn’t feel seen and that sounds like it was very painful,” and you just keep holding space for me. And I might cry because it just makes me so sad and I might shake my fist because I’m so angry, letting the bodily states come in. I can’t shake my fist at the investor in the meeting. 

If I have a chance to self-regulate with someone I trust later on, then something magical happens, then this stuff doesn’t build up and five, ten years in you don’t feel like all of a sudden your body is tense from so many different things, you don’t even know why, and you just need to lie down. And we call it — when really if you looked closely, we could trace it back — that it’s all these individual episodes of moments that haven’t been processed.

Matt: Let’s say that I had a friend who had been through something tough. How can I best hold space for them? 

Leo: The most important thing that you can do to a friend that’s going through a hard time is to offer what neuroscience calls warm accompaniment. It used to be called empathy but empathy has — it’s got a little — empathy is feeling what someone else feels, it doesn’t really encompass anymore what is meant or what makes it understandable.

So warm accompaniment means that you refrain from giving any advice, you’re not trying to fix anything. You’re not trying to tell them about your experience, you’re not saying, “Oh this reminds me of my time when I was sick,” you’re not trying to do anything but ideally — and this is from a practice that I also really enjoy called non-violent communication — you just offer back what you are hearing and that can be as simple as reflecting back the exact words. 

And that’s not always the right thing for people but if you’re just getting started, just saying — if you were doing this with me, Matt, if you said, “I had such a hard day at work,” for me to just say, “Wow, it sounds like it’s been a really hard day for you,” that is the warm accompaniment to be I am right there with you without being carried away by your experience. And so, reflecting back what you heard somebody say, noticing whether you can be present. 

You know, if you get carried away and you might say, “I also had such a hard day at work” and your day was so hard, now we’re not co-regulating. 

Matt: So I shouldn’t try to match it.

Leo: Right.

Matt: Should I say “I know how you feel?”

Leo: “I know how you feel” is sympathizing with another person, it is not warmly accompanying their experience. When someone is having a hard time, what is important to them is to understand, for their nervous system to understand that what they are feeling is okay. And I think that’s what you’re trying to say when you say “I know how you feel.” But more important is to offer up the reflection with warmth so that they can see “Yes, that’s what I’m feeling and this person is not triggered by this so I guess it must be okay and my body can relax a little bit.”

Matt: What are some other examples of warm reflection?

Leo: The main way we use to communicate as mammals is through the tone of voice. And there is a term in neuroscience called prosody that means the emotional content that your voice carries. And there’s thousands of nuances that we have in our voices to communicate how we are feeling without the information or the data of the words we are saying. So the most important thing that you can do is just to — the way you say, “Mmm,” or the way you say “Uh huh,” or the way you say “I get it,” — the emotional content of your voice is the most important signal of safety, and we want to do that with the resonance of our voice. 

And the best way I know how to do this is purely by understanding that you can stay present to cultivate that yourself, right? It’s hard, it’s gonna be hard for you. If you don’t know how to — 

Matt: It’s hard to listen.

Leo: Right? It’s hard to listen if you haven’t had enough listening from yourself for yourself or from somebody else for yourself so you can hold space. So that is the long-term practice. But looking into needs and feelings, guesses from the non-violent communication framework is a really wonderful, specific thing you can do. 

To say, “Are you feeling really upset because there wasn’t enough understanding in this meeting?” So that now the person has a chance to either say, “Yeah, you’re getting me,” and can expand, or can clarify what their experience is and accompany that warmly, and can say, “No, I’m not upset because I wanted understanding, I’m really upset because there is no harmony in this company.” A-ha, it’s not about understanding, it’s about harmony, right? And so now the closer — the more precise we can get to experiences, the more likely our nervous system can discharge this and let go of it.

Matt: The classic book on non-violent communication is by… is it Marshall Rosenberg?

Leo: Marshall Rosenberg, yeah, exactly.

Matt: I would particularly recommend it to anyone who is a manager because I think one of the most important things you can do as a manager is listen to people and really hear them.

Leo: Right, mhm.

Matt: And that’s very difficult. I think especially if you’re a new manager there is a temptation to make it about you.

Leo: Right. When you’re a manager and you haven’t done — All the sudden you work with people and you haven’t done your own inner work and your own inner training, it’s gonna be hard to hold space for people, which to a lot of people is a first when they first become managers. 

Matt: And that’s a lot of what I’ve been thinking about as well, is people who are becoming managers for the first time in distributed organizations. There’s lots of people who are freelancers but when you start to get to managing fifty, a hundred people, in a distributed fashion, there’s just not that much out there about it.

Leo: Totally. 

Matt: You’ve written about something called the loneliness spiral. Can you introduce that for the audience?

Leo: The loneliness spiral is associated with the fact that we have — as mammals evolved to be in groups, we are very unfit to survive alone. When we are alone for too long of a stretch of time many people report to feel a feeling that they name “I feel lonely.” And that feeling is simply our nervous system’s alarm system to say “Hey, if you spend too much time alone you’re not gonna survive in this world. Go make some friends, go be with family, go be with other humans.” And we need that physical touch, really in the same-room interaction for that, often for that feeling to dissipate. 

The problem with the loneliness spiral is not that we feel lonely, the problem is that often times when we feel lonely we feel scared at the same time. And actually even if I feel lonely, what I want to do is go out and meet friends, but if I feel scared now I start doing things, because I’m not able to hold that emotion very well in my body, I end up maybe sitting on the couch, eating more potato chips because that fills me up, and then watching some YouTube videos. 

Matt: It can distract you.

Leo: Exactly. So that can distract you but it’s not taking care of the underlying root cause. The thing that happens over time, if it’s not being acted on, parts of our brain — an author called Stephen Porges, who wrote a book called The Polyvagal Theory — he calls this heart of our nervous system the social engagement circuits. If they are not exercised through a muscle, through regular social engagements, through regular social contact — and this is one of my concerns with remote work — if that’s not exercised it atrophies.

Matt: So we’re talking right now.

Leo: Yeah.

Matt: It sounds pretty good, like you could be right next to me.

Leo: Right.

Matt: Does this also get activated by video calls, by phone calls, those sorts of things, Facetime?

Leo: It does, it does. That is good news for remote work.

Matt: That’s good. Because then I can connect with someone anywhere in the world.

Leo: It’s good news and, and I wonder if you’ve noticed this with remote work, is that most calls are scheduled, right? We are not here to just catch up, you know? We are not here to just tap me on the shoulder and say, “Hey Leo, how are you doing?” by the water cooler, “How was that concert you went to last night?” So the sort of social engagement that I’m talking about, that almost intimacy that can develop that happens most likely when things are unscheduled and spontaneous are much [less likely] to happen.

We have experimented with this at Buffer. We tried to have book clubs and social hangouts on Zoom and what not to create that. And I think that’s often what’s needed beyond the scheduled meetings where there is an agenda and you work through, and the informational content really is a thing, what it’s all about and not the emotional content that really is a thing that trains our nervous systems to know, “Okay, I’m not alone, there’s other humans that care about me, I care about them.” That thing.

Matt: How about if I’m in a crowd? I know personally sometimes I can feel very lonely even though I’m around a lot of people.

Leo: Right, yeah.

Matt: Just going to a coffee shop. But is that gonna help anyway?

Leo: It’s something. [laughs] It’s something but you can still feel very lonely. And my view on that from what I’ve learned about our inner states is that often that social engagement is activated only when we reveal something about ourselves, when we show something about our truth and about who we are. And that’s sometimes not very likely to happen in a coffee shop. You may walk around a lot of other humans but there is no heart to heart or there is no emotional connection. 

I think of the CTO at Product Hunt. His name is Andreas Klinger. He had a great suggestion. He said, “I think it’s a good idea for remote workers, wherever they live, to find other remote workers and to start small offices together so they could develop a group cohesion, even though they don’t really work together.” I love that.

Matt: A lot of folks listening to this are probably on one side or another of a one-on-one with a direct report or a manager. So what would be some good questions or things for people to do when they are in those meetings?

Leo: The most important question I think for a manager is to ask the person how they are doing. It’s colloquially so common to answer that with “fine.” 

Matt: It’s almost reflexive. If you said, “How are you doing?” I’d be like, “Yeah, good” or “Fine.” I wouldn’t even think about it really.

Leo: Right. Exactly.

Matt: Because it’s very vulnerable to answer something not — 

Leo: Right. So it becomes a question [of] how can you give people a chance to open up. The number one way I know how to do that is to give space to the other person to resolve things themselves. As a manager, the best thing you can do is train yourself to hold space for yourself so you are not having a million things that you need to unload onto your employee, to keep making more room, to keep letting more things bubble up that can be resolved. How do you feel about this? What do you — To keep it with open-ended questions and to let advice maybe only come in at the very end.

Matt: You cofounded one of the more prominent distributed companies. If you did another company, would you make it distributed again or do you think the in-person is more important?

Leo: I would probably not start distributed. For a sapling to grow I have this feeling that being in the same room together could be really, really vital, at least the first two people. 

Matt: I would actually — I think I would probably agree with that. WordPress, we were always distributed because it was open source. But for Automatic, the early folks, myself and Toni [Schneider], who joined as the CEO a few months after it started, we would see each other quite frequently in San Francisco. I was more based there at the time.

Leo: Right. So I think that early time, being together could be just extremely vital. And over time I think I feel I would be still excited to open that up and to make it fully remote as you go beyond ten people. And I would — remote work is a little bit like the Wild West. It has so many benefits, but there’s so much that’s not understood about the dynamics. 

I would probably be even more conscious about, first and foremost, my own coping strategies to working alone a lot and setting myself up much better. Often times the people that joined later, they were way better set up than people that were wanting to have a job at the company, they already had their families set up, they were happy to spend more time with their kids and at home. Often times they were better set up than me as one of the founders to like — that’s all over the place all the time. 

Matt: Let’s say we are doing a distributed company, we talked about some of the advice you’d have. Any other tips or things that you think from your experience folks in a distributed company, managers or founders, should think about?

Leo: Cultivating human-to-human connections as much as you can within the company. I had this one idea, I think what would be great is to have for these distributed companies in particular, to have a resident stress therapist that people could just go to and sit with for an hour and pour their heart out in relation to what is going on in the company so that they have some context. 

And then to meddle with the less productivity-related things when I believe — productivity is always about emotional states anyways. When we are not productive it’s because the task at hand has some emotional charge that stops us from doing it. You know, we are scared because of how people might receive this. A lot of people are scared of being successful and being seen because there is a lot of underlying trauma around actually being seen for what people do. 

So I think the reason when someone doesn’t want to do a task, there is some underlying emotional charge that’s not being taken care of and finding a way to get to that within a company through maybe a group activity, a regular structured or unstructured time where people can interact with each other, and to work with a manager, or to have a stress therapist or something like that, so that those aspects of your life that are often where you get stuck, they can get unstuck.

Matt: I’ve been asking everyone if you could imagine twenty years in the future, what percentage of jobs do you think are distributed or not in the office?

Leo: I would maybe say thirty percent. 

Matt: Thirty percent. All right, I appreciate it. Well, Leo, thank you again so much for joining me today. A lot of good tips. And you’ve given me a lot to think about.

Leo: Thank you so much for having me on, Matt, it’s been a real pleasure.

Matt: That was Leo Widrich, and you can find him on Twitter @LeoWid, or his personal site, powered by WordPress, leowid.com. If remote work is going to become the rule rather than the exception, we’re going to need to come up with ways to cope emotionally with our new social environments. Maybe it looks like regular team meetups, maybe it’s a hangout in virtual reality, maybe it’s co-working spaces with happy hours. Maybe if people feel less pressure to leave their hometowns to go work at employment hubs, they’d be able to maintain stronger ties with friends and family.

The solution is going to look like all these things and more. Whatever the future of work looks like, I’m glad that people like Leo are thinking about the psychological traps that might be easier to fall into when working from home. I know that the next time I start to feel a little lonely, I might plan to go grab a matcha latte with a friend, so my vagus nerve gets some exercise.

Read more about John Maeda in “Helping Creativity Happen from a Distance.”

John Maeda has spent the last three years leading Automattic’s design team, and on this episode of the Distributed podcast, he reflects on what he’s learned with our host, Matt Mullenweg. John shares how to facilitate collaborative creativity across a distributed team, explains why smart managers blog (and vlog) prolifically, and discusses how giving and receiving feedback with a spirit of gratitude, humility, and empathy is essential for managers, especially in a distributed context. 

The full episode transcript is below.

***

MATT MULLENWEG: What did real-time remote collaboration look like 30 years ago, in the primitive era before Slack and Zoom? My guest on this episode of the Distributed podcast knows, because he was there. 

Designer, author, and Automattician John Maeda spent the latter half of the 90s pioneering a new field called computational design at the MIT Media Lab, a legendary sandbox for researchers who wanted to explore and create the future of tech. Computational design was a bold new approach that applied design principles to the creation of hardware, software, and computer networks, and John helped define it from the beginning.

By 1999, John had developed enough of a reputation for Esquire magazine to name him one of the 21 most important people of the 21st century. Wired magazine once said that “Maeda is to design what Warren Buffett is to finance.” 

My company, Automattic, has been lucky to have John working with us for the last few years, and he will be moving to Publicis soon. He’s been leading a team of 70 designers scattered all over the world, and before he left, I wanted to talk to him about what that’s like, so I’m thrilled that he’s able to join me for a discussion about creative collaboration at a distance. 

We are here today with John Maeda, who leads what might be the largest all-distributed design teams, or at least that we know of. He is the author of three books, The Laws of Simplicity, which is actually what introduced me to John’s work, Creative Code, and Redesigning Leadership. And I believe there is a fourth book on the way, is that correct?

JOHN MAEDA: There is. It’s How To Speak Machine. And thanks for having me on.

MATT: Oh, no problem. So your title is Global Head of Computational Design & Inclusion.

JOHN: Mhm, mhm.

MATT: Computational design might be a concept that not that many people are familiar with as well. Tell us about that.

JOHN: Well actually, people ask me about that. That’s why I thought that How To Speak Machine is the first primer on that because when we think about the value of design right now, because of the technologies we use today, it isn’t a picture, it isn’t a clever drawing. If it’s computational, if it’s driven by code, or it’s tied to code, it can achieve scale, it can achieve behavior, it can be interactive. 

If you think of an early computational design system, that would be WordPress. It’s interactive, I can use it as a tool, it’s not like a poster in the MoMA collection, but it’s a usable system that is running with computation. It never gets tired. Want to add a post again? Okay. Want to add another post? Okay. 

So the computational system never gets tired. Whereas we’re in a room with a beautiful wooden table. This table, if we — we wouldn’t want to hurt this table, we don’t own this table, I know — but if we kept hitting at it, it would eventually fracture. It has physical laws. But computational systems behave differently because they are built out of programs.

MATT: Where do humans fit into this?

JOHN: Originally humans and computers interacted, like Hiroshi Ishii’s human-computer interface world.

MATT: Yeah.

JOHN: But now computers and computers interact, as you well know. They’re hanging out together without us, especially with AI. They’re hanging out. Like, “What do you got?” “I got this” or “I got that” “Well give me some of that.” So — 

MATT: I love the concept of the AIs that train against themselves. 

JOHN: Oh those are really cool.

MATT: Like the Alpha Go, [or] the other things where they have this adversarial learning against itself. So it can play hundreds of millions of games in a day.

JOHN: That concept you described used to be science fiction but now, because of the resources we have available to us by the cloud or everything we can buy now, that’s a normal thing. If our raw material has changed then design should have changed too vis-a-vis computer-based systems.

MATT: And has it?

JOHN: It’s trying to. That’s the one thing I’ve realized is so hard — this is across the tech ecosystem — is that there are a lot of designers who came from the past. And so when we look in this room, the person who designed the texture on that wall over there, that’s a kind of design, but it’s less relevant to the design of a new release of a new feature that needs something that actually has to ship right now. 

And the distance between that design and a design that once it’s shipped now has to iterate and improve at a rapid velocity — that’s a different kind of design. I think most of the design, maybe over 90%, is stuck in the old design, not in computational design. So that’s why I wanted to highlight that when I joined your merry band. 

MATT: Let’s say someone is listening to this, a younger person who is not currently in design and wants to go into it, and wants to be in this kind of present or future you’re describing. What should they work on?

JOHN: They should use WordPress. [laughter]

MATT: Okay, so that’s a good start.

JOHN: No, no actually not in that way. I have been using WordPress intensely, over two years now, getting on three, and it has really reminded me how the internet works. It has exposed the messiness of how information is transmitted, how it’s displayed on multiple platforms. 

It’s like people who really love WordPress will hate hearing this but it’s kind of like infants, for them to walk, there is this baby walker thing, I’m not sure if it’s legal anymore, but there’s this thing where the baby can stand up in this walker thing and they can move, they can move around the room and it’s like, “Wow the baby is moving around.”

MATT: It’s like a little circular thing with wheels?

JOHN: A circular thing with wheels on the bottom, exactly.

MATT: I haven’t seen one of those recently but I know what you’re talking about. 

JOHN: They must be illegal now for some dangerous reason. But to me it’s been like a baby walker because — I know a lot of the high tech stuff but I lost sense of the basics in many ways. 

MATT: What are some of those basics that people should be familiar with?

JOHN: The basics are, first of all, collaboration.

MATT: That’s not a basic. That’s hard!

JOHN: Well I mean that’s a basic that comes — if you build software yourself you don’t have to collaborate, right? But by having a distributed system you have to collaborate. So just to get in touch with that, that’s been great.

MATT: What makes you good at collaboration?

JOHN: Listening. I think it’s the number one important thing is listening. What is the saying, two ears, one mouth? So two-to-one? [laughs] 

MATT: But everyone can’t do that at the same time.

JOHN: Oh yeah. 

MATT: Sometimes it’s going to be impossible?

JOHN: Yeah. The collaboration thing is key, the listening part. The second thing is being technically facile. Being able to write poetry in code. I think for a long time, because I was in the classical design world where coding is bad, like coming back into, via Kleiner Perkins and eBay and Automattic, I’m like, “Oh, coding is good.” And why is it good? It’s because you have agency. What does “creative” mean? It means I’m creating. And if you can code you can do so many things. 

So collaboration is important and to be able to make code is great. The thing I love is how I think of what I’ve learned with WordPress — it’s like Lego. And people will say, “Oh it’s just Lego, it’s not like real wood, real marble, real concrete, it’s just Lego.” But in this world of having an idea, an MVP or an MLVP, you want Lego to be able to make ideas spun up quickly. 

MATT: You brought it full circle. You said community-made platforms win or lose. Some people say that WordPress is not the best CMS, but it does have one of the largest communities and has been the most successful.

JOHN: Yeah.

MATT: You also said that the first thing that designers need to know is collaboration. 

JOHN: Yes.

MATT: So it came to people.

JOHN: Yeah.

MATT: As we said in the intro, you lead definitely one of the larger all-distributed design teams. So if collaboration is important for design and you can’t have everyone in the same room around a whiteboard, what do you do? What are the challenges? And what are some of the benefits?

JOHN: You just reminded me how in the early 2000s or late ’90s I had made this system called Design By Numbers, and it was a system to teach anyone how to code. It was very limited. You could only draw in a 100 by 100 square in black and white. Super constrained system, super easy to teach anyone computation. And then two people on the research team, Casey Reas and Ben Fry, who were involved with this system, said, “I think this system should be less constrained. It should be color. And why is it limited to 100 by 100?” 

And so they built this system called Processing and they did two things. The first is they built a community center portal around it and the second thing they did was they open-sourced it. And at the time I’m like, “That’s never going to take off. That’s just sort of a — what is this? It’s never going to happen. You should be working on something else.” And that’s why I never really believe anything I say because I could be wrong. I was so glad they didn’t listen to me and they went off and made this Processing thing. And I think there’s a gazillion books about it, there’s communities around it.

MATT: It’s extremely popular, yes.

JOHN: I had to learn from them the power of community because I spent most of my career making software by myself. Everything I made by myself, I designed every book by myself because that’s what I thought people did. The great creators made things by themselves.

MATT: Which is also amazing because, as you know, so many great artists had workshops, architects…

JOHN:  I know, I didn’t know that. I didn’t know that Michelangelo didn’t paint all those. 

MATT: Leonardo da Vinci… 

JOHN: I didn’t know that.

MATT: Raphael. Yeah.

JOHN: Well, you know, I grew up with —  

MATT: Today, Jeff Koons.

JOHN: — my family had no education, we had no books, there wasn’t internet, I had no idea.

MATT: The myth of a solo creator might be one of the most corrosive to creativity in general actually.

JOHN: Ohh totally. Oh my gosh. I almost died doing that. I got sick, overworked, I was in the hospital for three weeks. I went over the line, you know?

MATT: You told me about that before to caution me against it.

JOHN: Oh yeah, it happens, it happens. It goes past… 

MATT: I appreciate those cautionary tales. It’s worth noting on this podcast itself is not a solo endeavor.  

JOHN: I agree 100% and I think that the solo creator myth is something that I strive to break through sharing my own embarrassing failures around this. And then when working with teams the number one important thing that I found is respect.

MATT: In working together over these past few years you seem to exhibit an incredible amount of empathy, which is also important for design. Maybe we’ll add that to the list. Or I’ll put it on my list, you don’t have to put it on yours. How do you balance that empathy with that, [so you’re] able to get through these tough things?

JOHN: One of my favorite artworks I’ve made in my life — I don’t have many things I like that I did, but I was in a meeting at MIT where I was having this feeling of, “Whoa, this is feeling really ugh, you know?” I calligraphed on a piece of paper “thicker skin” 75 times. And it’s entitled “Thicker Skin 75 Times.” And it was sold at an auction for charity for UNICEF in Paris. But it’s my proudest piece of artwork because all of my feeling went into that simple drawing to remind myself that it really isn’t about them, it’s about me: Can I have thicker skin?

MATT: It’s a powerful concept.

JOHN: Yes. But it hurts still. It hurts. If there is someone that you really respect and doesn’t respect you, sometimes it works, sometimes it doesn’t. Does it hurt? Of course. Every time it hurts. Like, “Oh wow.” You let someone down and you don’t forget it.

MATT: But does that close you off to the full range of human emotions?

JOHN: That’s more a combination of thicker skin and gratitude.

MATT: Gratitude, okay, that’s one we haven’t talked about yet.

JOHN: Yes, thicker skin is there if you’re feeling bad and then the gratitude is there because it’s like, “This is an awesome world, like, this is so amazing.” Or you’ll feel gratitude for someone in your past and that activates something good in you. I always think about how I would not be where I am today if it wasn’t for my 11th grade high school chemistry teacher, Mr. Wakefield, who took an interest in me as being the number two smart kid in his class. 

The number one kid was so much smarter but came from a really good background whereas I came from a background where I knew nothing. My parents had no education, we didn’t know what the future should be like. I was working after school at my parents’ shop, on the weekends. I hated summers because I had to work there all the time. And so Mr. Wakefield said to me, “You want to go to a good school, you’ve got to have stuff on your application that makes you credible.”

MATT: The extracurriculars?

JOHN: And I was like, “What’s that?” So he said, “We’ll make a science club,” and whatever, so we did that. And then he said, “You need to take a class at the local university over the summer.” And I said, “Oh my parents won’t let me do that because I have to work at the store.” And then Mr. Wakefield came to the store on Saturday, on the weekend, to talk to my parents. 

MATT: Wow.

JOHN: He didn’t have to do that. He was a retired Boeing engineer, he never would venture into the Chinatown area. I mean he didn’t quite fit the whole thing. [laughs] He came and talked to my parents and said, “You want your son to go to a great university, let him take the summer off and do this, give it to him.” And they did. 

MATT: And they did. What did you study that summer?

JOHN: Organic chemistry. I loved chemistry. I was going to become a chemist. I was almost going to be — at MIT the only class I didn’t fail out of in the first year — it was a really bad year — was solid state chemistry. I got one of these rainbow stickers on my tests. Oh it’s the one moment of “Ohh, I’m not an imposter. Should I be here?” I got the golden sticker that one time.

I think of Mr. Wakefield, I think of other people like that who gave me a chance and I feel gratitude towards them. And then it gets easy, like how can I serve you, how can I help you? It’s easier.

MATT: One area we didn’t fully cover was that chemistry for teams or the collaboration for design teams. In a remote setting does anything stand out?

JOHN: Oh my gosh, so this is all about distributed collaboration so I know — exchanges around commentary on code and ASCII text, etcetera, some images, some pull request is initiated, it goes through the shipping — I think of GitHub or GitLab or any of these systems, like a big ship construction site where the ship is going through this gigantic tunnel about to launch out there.

For developers it is highly developed but for designers it’s not developed. That’s why I think things like Figma are so popular because they closely emulate high-network collaborative spaces that remove the abstraction between storage and actual application. [It’s] super reliable, it runs fast and is social to the extent that it’s not actually annoying like Slack can be sometimes. [laughs]

MATT: Why can Slack be annoying?

JOHN: Slack? Oh my gosh. Slack can be annoying for so many reasons. And some people say to me, oh well you’re not Gen Z or Millennial so you don’t get it. I’m sorry, but I think I have been able to Slack with the best of them. 

MATT: I’d say you’re a pretty big Slacker.

JOHN: I know, I try. I try to be a good Slacker. But the feeling I have around a system like Slack is that it moves things so quickly that you can’t think fast enough. And a quanta is so small, the message size is so small. And if the organization is a six-person start up — I think Slack is fantastic, but anything larger — it isn’t about the message, it’s about the feeling. Like, how are you feeling for yourself as a leader of all these people? You need to get a sense of how they feel. And from a Slack instance you can’t get that sense of feeling unless someone is really good at choosing the right emoji, you have no idea, is this the real reaction? You can’t tell. 

MATT: I know creative work — I think creative work requires uninterrupted periods of time, of focus.

JOHN: That’s a good hypothesis. I think you’re right. Yes, you’re right because one of my favorite metaphors is by the late Gordon MacKenzie, and it’s about how he draws a graph — a graph across the — a horizontal line, and then the majority of the line is called “making milk time,” and the end point of the line is “expressing the milk.” 

So a cow is sitting there eating, and you’re like, “Come on, cow, give me milk. Give me milk, cow, give me milk.” And then, “Where’s the milk, cow?” And the cow is just sitting there, chewing the grass. And it’s like, “This cow is not working.” But actually the cow is making the milk but the cow is only rewarded when they express the milk. The example is about how creative work takes eating-grass time and sitting in the sun, otherwise all you get is barely made milk.

MATT: And you’re leading 75-80 people around the world, 24/7. 

JOHN: Mhm.

MATT: How do you find that making-milk time?

JOHN: Because we’re distributed and because we have all kinds of teams that work with designers, I think it’s up to the local zone of leadership to be able to create that time. The best that I can do is a round robin, asking, “What’s up, what are you doing, what are you doing outside of work?” And then someone will say to me, “But that’s not work.” And I’ll say, “It’s your work as a creative person to express yourself.”

So one thing I’m really happy about is our blog, Automatic.design. You may remember in the beginning it was hard to get off the ground because some designers felt like, “Well why am I going to blog? What is the point of blogging? What’s that for?” And my point is blogging is good for you. It’s mental health, it’s expression, it’s sharing your process with the world. And when you relate to the world, your standard of quality floats to that value of the world. It’s a market economy of ideas and by putting ourselves out there, you become relevant.

MATT: I’ve noticed, talking about that low-bandwidth communication of text, downsize to Slack.

JOHN: Yeah.

MATT: You internally and now externally are on your YouTube channel.

JOHN: I’m doing YouTube, I’m a YouTuber now. Oh my gosh, I love it.

MATT: Yeah, you create a lot of these videos.

JOHN: I do. 

MATT: And I also perceive that you’ve literally created a lot of videos. You edit a lot, you insert emojis.

JOHN: I make the whole — It is the classical “I make it by myself thank you very much.” [laughs] 

MATT: Yes, so why are you using video to communicate? 

JOHN: Oh my gosh.

MATT: Internally as well. We have so many different tools.

JOHN: Look at you. You’re a WordPress-world person, you’re speaking into a metal thing, holding it with your hand, you’re not typing, you’re audio casting. So you see the diversity of the ecosystem. So YouTube to me represents really what the younger generation has figured out, is [it’s] so much more convenient.

MATT: Should managers at distributed companies or leaders learn video editing?

JOHN: A thousand, thousand percent yes. Because editing skills are ways to communicate in the same way that blogging is, but be careful to add a closed-caption, subtitled track because that makes it even more inclusive for those who have problems understanding spoken English, or for a language barrier.

MATT: One thing that’s cool, and actually one of the features I’m most excited about, is just launching. Our internal video player just launched — 

JOHN: Oh yeah, congrats, yeah that was good.

MATT:  — the speed thing.

JOHN: That’s important.

MATT: Which YouTube has had forever. So you can speed things up or slow them down.

JOHN: Yes.

MATT: I’ve found it’s interesting for meetings. What might be a synchronous status meeting that might take 15 minutes  —

JOHN: Yeah, you could —  

MATT: You can get through in ten minutes or eight minutes depending on your speed of processing.

JOHN: Whoa. You can express it.

MATT: Especially people who listen to the podcast, I imagine more than half, if not more, are listening to this sped up right now.

JOHN: That is wild.

MATT: So you actually train yourselves to be able to listen faster. 

JOHN: Oh that’s so interesting.

MATT: And I wonder if I can improve efficiency.

JOHN: Well one thing I’m doing with the team around me is my direct reports, on Monday, and you don’t know this, but Monday what we do is I have a one-minute video requirement. On Monday you post your one-minute video and that’s your stand-up, but it’s async. And that way you can comment on the video. Any extra comment can happen by text. But you can also hear it in full fidelity how someone is experiencing their life and their work.

MATT: That’s really interesting.

JOHN: It’s an async stand-up.

MATT: What are some other things you do in leading the team? I know you have a Monday, Tuesday, Wednesday publishing schedule.

JOHN: Yes I do, yes.

MATT: Tell us about that and more. 

JOHN: Okay. One thing I’m really excited about is learning the distributed universe and how hard it is to have a point of reference. If you work at a physical place, you walk in, you can tell the seasons, there is a Monday, there is a Friday. Monday feels so different than a Friday on-prem. So you lose your sense of gravity. There is that Sandra Bullock film — was it Gravity? Where she’s floating in outer space and it’s “Which way is up, which way is down?”

So one thing that I developed after a lot of feedback — I love feedback — every negative or positive feedback I’ll share internally, just with everyone, because it’s easier that way. If people want to talk about me, they have already talked about me because I’ve shared it and it’s easy. But one of the feedback points I got was that I was posting or sharing too much information. And then I realized, well maybe it’s because I haven’t given it structure. So I gave it structure. 

But then I realized that structure isn’t as good as time structure. Because time creates gravity in a distributed organization. So Monday’s post is about the external world, the external realities, Tuesday’s post is about business, and Wednesday’s post is about organization. And I limit myself to posting in that cadence. People expect Monday to be a certain thing, Tuesday, Wednesday. 

The other practice I developed in the team around me is I borrowed a technique developed by Joel Califa, he’s a designer I used to mentor, but now these people who I mentored are like my teacher[s]. It’s a spreadsheet where everyone posts what they’re going to do that week and then they rate how that goal has been achieved during the week. It’s like an old-style Japanese office-memo thing. And the reason I use a Google Sheet and not a special tool is because everyone authenticates. There’s no “Hey can I get a login, can I get a login?”

MATT: Yeah. At our company everyone has a Google account.

JOHN: Yeah, and that Sheet is open to everyone in the company too. I love the idea of transparency that you brought into the Automattic culture or created with your team members over these years. And I think transparency is so important but clarity also is key.

MATT: You said that you love feedback. Positive, negative, you love sharing it.

JOHN: Yes, I do. It’s good.

MATT: What do you think engenders a healthy culture? Does everyone on your team take that same approach? And how do you judge a healthy culture of feedback?

JOHN: I’m laughing because the best feedback is delivered non-anonymously.

MATT: I know you feel very strongly about that.

JOHN: For me I feel strongly about this because when you deliver it non-anonymously you can understand it better. I have two favorite sayings and they’re too long so I can’t memorize them. But one of them is by Coach Pat Summitt, and paraphrasing, “When you’re able to give someone straight feedback you’re showing them the compliment that they will be able to take it.” 

And so when people give me feedback, does it sting that I am no good at something? Yes. I’m like whoa, I thought I was good at that. And I might think they’re wrong. But then when they say how I didn’t achieve something I’m like, “No, you’re right, I could improve there.” If you get it anonymously you don’t know the smell or taste of it. It’s like if I gave you —  

MATT: It’s missing context, for sure, yeah.

JOHN: It’s missing — You have to fill in the rest of the story 80 percent.

MATT: It also seems you can’t get any anonymous follow-up on it?

JOHN: Well you can tell everyone “I got anonymous feedback, this is what I’m doing.” And then you give more power to anonymous people and those who actually give you the — 

MATT: But you share all the feedback, anonymous or not, right?

JOHN: I do, yes. And one of my proudest achievements is the anonymous feedback and the in-name feedback is just as bad. [laughter] 

MATT: So people are comfortable saying it either way.

JOHN: Right, right. 

MATT: You also work a lot on inclusion.

JOHN: Mhm.

MATT: That’s from a position of privilege as well.

JOHN: Absolutely and I —  

MATT: You’re very powerful and you’re John Maeda. 

JOHN: People think that I’m something. An octopus, like, whatever. But that’s why a lot of what I do is reiterate that I’m only as good as what I do now.

MATT: How do you make people who might feel that they don’t have that privilege to give things to you directly, how do you make them comfortable with that? 

JOHN: I haven’t cracked that one yet but it’s on my list of… how do I invite them into the fact that my only goal is to serve others and I cannot do that unless — think of all the user research. Unless I have high-fidelity user research, how am I going to improve? Maybe my goal is to center on that concept with more people that I do believe in agile development, I’m a computational system, organic, [laughter] and how am I going to iterate and improve if I don’t get really high-fidelity feedback? 

Maybe I might become much more open to delegation of that. Because there are some people who feel that I’m in a privileged position and some people feel privileged enough to go straight with me. Like if you don’t feel comfortable with me, talk to them and I could just anoint that role —  

MATT: But then you lose the fidelity.

JOHN: I do. And then I also do recognize that there are those who will always feel something. And it’s often not about me, it’s someone like me that in their past [with whom] they had a bad experience. So I totally understand why there would be no reason that they feel that they could be candid with me, because something bad happened in the past.

MATT: Are you also that candid with everyone you work with?

JOHN: Am I that candid? It depends. 

MATT: Can everyone handle that kind of raw — 

JOHN: That’s the challenge of getting older for me. When I was younger, I would tell everyone everything I thought. Oh my gosh, people couldn’t stand me, for good reason. I mean it was okay, I forgive them. Actually I hope that they forgive me. I would just tell them what I think and I was direct all the time. 

And then I realized wow, this is not working. This is not working. I believe in the “I’ll show you respect by telling you what I think.” But it’s like, “No, actually he doesn’t want to hear what I had to say. Whoops.” So I changed. 

MATT: Why is it bad if people are doing the same to you, not giving you the direct feedback?

JOHN: With people who I develop a strong working relationship with, then they are the ones who ask me, “Can I get your feedback.”

MATT: So conversely they feel more comfortable with the raw feedback from you?

JOHN: Yeah. And some instances, some people want that, some people can, quote, “handle it,” which means that they were privileged in some way where that became — where that’s doable. But there are some who just had a really difficult life that they just don’t want to handle that and it just hurts them in a way, it doesn’t help them. And so I’ve become much more conscious of “Huh, how do I adapt to what you need?”

MATT: In design you are also overseeing everything that goes out to all of our users.

JOHN: Mhm.

MATT: Everything we’ve been saying about feedback is pretty universal. Is there anything specific to distributed [work] that you want to throw in there? 

JOHN: In a distributed organization I think that the value of it is that you can now control your life differently. I know so many people [for whom] distributed work has been able to make them better parents, better children to their parents as caregivers. Them coming from that point of view is the beginning of recognizing that this is an amazing job to have. And do you enjoy that aspect of those jobs? Yes. Great. Now what kind of work are we doing and how can we safeguard that wonderful thing that you are able to do because of this paradigm. 

That’s what interests me the most, is that it’s a really special thing to be able to work distributed, and if you can start from the respect of that versus the wonder of it, then you have hard conversations about, “Now what should we do with the work to safeguard that?”

MATT: Tell me about your ideal work space.

JOHN: My ideal work space — I’m still QWERTY, we’re talking typewriter-speak. How do you say the other one?

MATT: Dvorak?

JOHN: Thank you. I don’t know how to pronounce it. Dvorak. I love a Kinesis keyboard because it has helped me I think —  

MATT: Those are the curved ones, right?

JOHN: It’s the curved one. In my late twenties I had really bad RSI. It’s the way I hold my body, but that really helps. I like to have that nearby. I like it super quiet. I don’t like to put headphones on, it’s a bit constraining.

MATT: Do you put music on?

JOHN: No music, no music, but hopefully art around to distract me.

MATT: Besides the Kinesis, any must-have equipment? I think you use a custom camera, right?

JOHN: Oh my gosh, I have fallen in love with this new thing. You know how headset experimentation is so important for distributed? It’s almost like a hairstyle problem. I found that in-ear musician-quality microphone monitor headphones, they’re great because they —  

MATT: Did you do the custom?

JOHN: There is this memory tip cushion thing that you can get that is super comfortable, sound-isolating. For audio quality it’s fantastic. 

MATT: That’s amazing.

JOHN: I love good microphones. Podcast-quality microphones, the sound quality is so much better. I do love the Sennheiser headset for sound-isolation quality. Like, we can be talking and I’d be in the airport, and you’re like, I don’t hear anything.

MATT: Oh yeah. 

JOHN: That’s bizarre how well that works.

MATT: Noise-cancelling not for you ears, for the mic. A noise-cancelling mic.

JOHN: That’s bizarre how good that is. But I do always feel a little embarrassed wearing it. You have no problem being in a restaurant wearing it. [laughter]

MATT: No, you look like you’re in a call center or something.

JOHN: I can’t go there. You wear it all the — I can’t do that. Yeah.

MATT: Zoom, Hangouts, Skype? What’s your go-to?

JOHN: Oh my gosh I can’t stand all of them. I like audio-only if I can. I like phone, yeah. 

MATT: Hmm. So you make phone calls?

JOHN: I make phone calls, yeah. It feels good. 

MATT: What’s your number-one tip for getting things done?

JOHN: Is if you’re lucky to have a good assistant, and if you are less lucky, having any good to-do note system, they always work. So the competency of making a list, oh, so good.

MATT: One thing I love about working with you is you’re go, go, go. 

JOHN: Aww.

MATT: What is your drive there?

JOHN: My parents worked so hard all their lives. I think about my father. He’s 84 years old, he’s hunched over, he can’t stand up straight, because he was carrying so many heavy things all his life. My mother, because of the cold water involved in tofu — her hands — she can’t feel anything. They worked extraordinarily hard. They are an example that was set that tells me I should do more. 

MATT: What are some of your habits that contribute to that, good and bad habits?

JOHN: I’m not good at vacationing. As you know, it’s not my forte. 

MATT: That was a goal for the year. 

JOHN: You gave me feedback and I took it, and I was like, “Okay, I’ll do this vacation thing.”

MATT: Although I think you worked the whole time.

JOHN: I had to get stuff done. [laughter] But vacation, not good at. I don’t read enough. You read a lot. You’re always reading. I don’t read enough.

MATT: You probably read all day. Do you mean books?

JOHN: Books, books. I’m consuming information. But I want to get good at reading books.

MATT: And finally, 20 years from now, what percentage of jobs do you think will be distributed?

JOHN: I think for developers, I think it will become a norm. I think for whatever we think of for designers it will be 50/50. Fifty for designers who are doing much more of the traditional creative, emotional type of work that requires more high-bandwidth collaboration, but it’s going to be expensive, that work. But the other half is all going to be computational.

MATT: Well, thank you so much, John.

JOHN: Thank you. This was fun.

MATT: That was John Maeda. You can follow him on Twitter at @johnmaeda. That’s J-O-H-N M-A-E-D-A. 

Slack is a tool that’s so widely used it feels ubiquitous in the tech world. And when everyone uses a tool, sometimes it can be difficult to imagine how it might be improved, or how a different tool might be better. It’s a privilege to hear someone like John Maeda — someone who has spent much of his long career thinking about digital interfaces — dissect the technology and talk about the way that it works, and where it falls short.

Hearing about the live-video-chat-meets-virtual-whiteboard tool John helped create in the 90s makes me think about how distributed design teams might use that today. It’s a great reminder that devices and interfaces can always be iterated on, which is both a great lesson from computational design and one of the great pleasures of building digital tools.

John has a humble, thoughtful approach to distributed collaboration, and thinks about how humans operate as much as how computers do. When you’re working with people across the globe, sometimes the best collaborative tools are the oldest, like listening, gratitude, and empathy. 

John’s time with Automattic will be coming to a close soon — he’s accepted an exciting new role with consulting firm Publicis Sapient — but I hope that his thoughtful and humble approach to distributed collaboration will live on in our design team, and I look forward to him contributing to Automattic as an adviser.

Next time on the Distributed podcast, we’ll be talking with Leo Widrich. Leo helped build a successful distributed startup called Buffer, and was living the Bay Area dream. But he felt something was missing from his life, so he quit his job and turned to ancient wisdom and mindfulness to achieve emotional resilience. We’ll hear Leo’s story, and learn how distributed workers can avoid the psychological pitfalls that are unique to working remotely.

Thanks for joining us.